Ammonia → 2-Amino-4,5-dimethoxybenzamide

HRID 359534Notes

Reaction equation

HRID 359534 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4](O)=[O:5].C(N1C=CN=C1)([N:17]1C=CN=C1)=O.O1CCCC1.N>O>[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([NH2:17])=[O:5]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 797364,5-Dimethoxyanthranilic acid

Product 1

HCID 108672362-Amino-4,5-dimethoxybenzamideYield 23.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 23.7 g of 2-amino-4,5-dimethoxybenzoic acid, 19.5 g of 1,1'-carbonyldiimidazole and 600 ml of tetrahydrofuran Was stirred for 2 hours at room temperature and then saturated with anhydrous ammonia with ice bath cooling. After 24 hours, the reaction mixture was diluted with 50 ml of water, heated at reflux for 2 hours and then concentrated under reduced pressure to about 50 ml. This liquid was mixed with 100 ml of 0.1N sodium hydroxide and then extracted with three 200 ml portions of dichloromethane. The extracts were combined, dried and evaporated. The residue was crystallized from acetonitrile, giving 5.5 g of 2-amino-4,5-dimethoxybenzamide as light grey crystals, mp 135°-138° C.

Workup

  1. waitAfter 24 hours
  2. temperatureheated
  3. temperatureat reflux for 2 hours
  4. concentrationconcentrated under reduced pressure to about 50 ml
  5. additionThis liquid was mixed with 100 ml of 0.1N sodium hydroxide
  6. extractionextracted with three 200 ml portions of dichloromethane
  7. customdried
  8. customevaporated
  9. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-cf73fa4c132f4db99e9db4fc049b8e43
Source dataset
uspto-grants-1991_03
Patent number
US05001157

Reaction notes

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