تفاعل #1162935

معادلة التفاعل

4-hydroxy-1,5-naphthyridine-3-carbonyl chloride hydrochloride

2-p-hydroxyphenylglycine

dichloromethane

trimethylchlorosilane

→

α-(4-hydroxy-1,5-napthyridine-3-carboxamido)-p-hydroxyphenylacetic acid

المذيبات

triethylamine

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added
2. 2
   درجة الحرارةthe resulting mixture was refluxed for 20 minutes
3. 3
   درجة الحرارةwhile cooling with ice for 4 hours
4. 4
   تركيزThe reaction mixture was concentrated under reduced pressure, 50 ml of water
5. 5
   workup.ADDITIONwere added to the residue
6. 6
   ترشيحThe precipitated crystals were collected by filtration
7. 7
   workup.ADDITIONpotassium carbonate was added
8. 8
   أخرىAfter removal of insoluble materials
9. 9
   ترشيحby filtration
10. 10
    ترشيحThe precipitated crystals were collected by filtration
11. 11
    غسيلwashed with water
12. 12
    أخرىdried

الإجراء التجريبي

To a mixture of 1.35 g of DL- 2-p-hydroxyphenylglycine, 50 ml of anhydrous dichloromethane and 4.05 of triethylamine, 2.62 g of trimethylchlorosilane were added, and the resulting mixture was refluxed for 20 minutes. After the addition of 2.1 g of 4-hydroxy-1,5-naphthyridine-3-carbonyl chloride hydrochloride, the reaction was effected while cooling with ice for 4 hours. The reaction mixture was concentrated under reduced pressure, 50 ml of water were added to the residue, and the resulting mixture was adjusted to pH 1 with 4N hydrochloric acid. The precipitated crystals were collected by filtration, suspended in 50 ml of water and potassium carbonate was added thereto. After removal of insoluble materials by filtration, the filtrate was adjusted to pH 1. The precipitated crystals were collected by filtration, washed with water and dried to give 2.1 g of DL-α-(4-hydroxy-1,5-napthyridine-3-carboxamido)-p-hydroxyphenylacetic acid. M.P. 310° to 320°C (decomp.)

المصدر