تفاعل #816416

معادلة التفاعل

13

N-acetyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

hydrazine hydrate

→

compound 14

المردود 86.8%

N-acetyl-7-amino-1,2,3,4-tetrahydroisoquinoline

المردود 86.8%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةunder refluxing for 20 minutes
2. 2
   درجة الحرارةthe mixture is refluxed for an additional 4 h
3. 3
   درجة الحرارةcooled
4. 4
   ترشيحfiltered
5. 5
   غسيلthe residue washed with methanol
6. 6
   تركيزThe filtrate is concentrated in vacuo
7. 7
   أخرىthe residue recrystallized from EtOAc

الإجراء التجريبي

A mixture of 13 (5.1 g, 23 mmol), activated carbon (4.2 g), ferric chloride hexahydrate (2.1 g, 7.6 mmol) and methanol (140 ml) is stirred under refluxing for 20 minutes. To the boiling mixture is added hydrazine hydrate (8.5 g, 265 mmol) dropwise, and the mixture is refluxed for an additional 4 h, cooled and filtered and the residue washed with methanol. The filtrate is concentrated in vacuo and the residue recrystallized from EtOAc to give compound 14 (3.8 g, 85% yield). 1H NMR [300 MHz, (CD3)2SO], a 3:2 mixture of amide conformers doubling most signals, δ 6.80 (1H, d, H-5), 6.40 (1H, d, H-6), 6.33 (1H, s, H-7), 4.89 (2H, br s, NH2), 4.46 (0.8H, s, ArCH2N), 4.41 (1.2H, s, ArCH2N), 3.57 (2H, t, ArCH2CH2N), 2.66 (1.2H, t, ArCH2CH2N), 2.55 (0.8H, t, ArCH2CH2N), 2.06 (1.2H, s, COCH3), 2.05 (1.8H, s COCH3).

المصدر