Ammonium Chloride → 3,5-Diaminobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester

HRID 1250802Notes

Reaction equation

HRID 1250802 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[C:29]([CH:31]=[CH:32][C:33]([O:35][CH3:36])=[O:34])[CH:28]=[CH:27][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13](=[O:26])[C:14]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[C:16]([N+:23]([O-])=O)[CH:15]=1.[Cl-].[NH4+].CO.O>[Zn].CO>[CH3:1][O:2][C:3]1[CH:30]=[C:29]([CH:31]=[CH:32][C:33]([O:35][CH3:36])=[O:34])[CH:28]=[CH:27][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13](=[O:26])[C:14]1[CH:19]=[C:18]([NH2:20])[CH:17]=[C:16]([NH2:23])[CH:15]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 22242641Methanol--water (1/1)HCID 543196263,5-Dinitrobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester

Product 1

HCID 537693143,5-Diaminobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl esterYield 95.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

1.0 g (1.99 mmol) of 3,5-dinitrobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester and 0.42 g (7.96 mmol) of ammonium chloride were suspended in 20 ml of a mixture consisting of methanol : water 9:1. 2.6 g (39.8 mmol) of zinc were then added in portions in the course of 30 minutes. After 2 hours at room temperature 20 ml of methanol were added. After a further 17 hours the reaction suspension was partitioned between methylene chloride and water and the organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water. The organic phase was then dried over magnesium sulphate, filtered and concentrated by evaporation. Chromatography of the residue on 150 g of silica gel using ethyl acetate yielded 0.84 g of 3,5-diaminobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester.

Workup

  1. customAfter a further 17 hours the reaction suspension was partitioned between methylene chloride and water
  2. washthe organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water
  3. dry with materialThe organic phase was then dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-a6c803cc468640bf9119c68da1930e4c
Source dataset
uspto-grants-2002_01
Patent number
US06340506B1

Reaction notes

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