Reaction #1583867

Reaction equation

dimethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

NaOH

→

title product

Yield 57.2%

5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

Yield 57.2%

Solvents

methanol

methanol

Conditions

Workup

1. 1
   Otherwas conducted at 70° C.
2. 2
   workup.STIRRINGunder violent stirring for 6 hours
3. 3
   Otherevaporated under reduced pressure
4. 4
   Otherto remove 80 mL methanol
5. 5
   workup.ADDITIONTo the residue was added 200 mL water
6. 6
   OtherThe unreacted starting materials are removed by filtration
7. 7
   Otherto separate a yellow solid, which
8. 8
   Filtrationwas filtered
9. 9
   Otherdried
10. 10
    Otherto produce a khaki powder

Procedure

3.5 g dimethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (0.01 mol) and 150 mL methanol were mixed. To the mixture was added a saturated aqueous NaOH solution (9 g, 0.225 mol) under stirring. The reaction was conducted at 70° C. under violent stirring for 6 hours, and evaporated under reduced pressure to remove 80 mL methanol. To the residue was added 200 mL water. The unreacted starting materials are removed by filtration. The filtrate was adjusted to a pH of about 2.5 with 1 mol/L hydrochloric acid to separate a yellow solid, which was filtered and dried to produce a khaki powder. The resulting powder was treated with methanol to produce the title product as a yellow solid (1.9 g) in a yield of 57.2%.

Source