Ammonium Chloride → Methyl 2-amino-5-ethoxy-4-methoxybenzoate

HRID 1595732Notes

Reaction equation

HRID 1595732 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([O:17][CH3:18])=[CH:6][C:7]([N+:14]([O-])=O)=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])[CH3:2].[Cl-].[NH4+]>O.CO.[Fe]>[NH2:14][C:7]1[CH:6]=[C:5]([O:17][CH3:18])[C:4]([O:3][CH2:1][CH3:2])=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 2

HCID 25517Ammonium Chloride2×HCID 10587106Methyl 5-ethoxy-4-methoxy-2-nitrobenzoate

Product 1

HCID 10585283Methyl 2-amino-5-ethoxy-4-methoxybenzoate

Reagents, catalysts & solvents 3

HCID 23925IronCatalyst3×HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 17.0 g (66.7 mmol) of methyl 5-ethoxy-4-methoxy-2-nitrobenzoate, 13.1 g (233 mmol) of powdered iron and 17.7 g (334 mmol) of ammonium chloride in 95 mL of water and 245 mL of methanol was refluxed for 4.5 h. An additional 13.1 g of iron was added followed by refluxing for 2.5 h. Then an additional 13.1 g of iron and 17.7 g of ammonium chloride was added and refluxing was continued for 12 h. The reaction was filtered through Celite and methanol was removed from the filtrate. The filtrate was extracted with chloroform and the extracts were treated with Darco, evaporated and dried in vacuo (50° C.). The yield was 11.0 g of methyl 2-amino-5-ethoxy-4-methoxybenzoate as tan crystals: mass spectrum (electrospray, m/e): M+H 225.9.

Workup

  1. temperaturewas refluxed for 4.5 h
  2. temperatureby refluxing for 2.5 h
  3. temperaturerefluxing
  4. filtrationThe reaction was filtered through Celite and methanol
  5. customwas removed from the filtrate
  6. extractionThe filtrate was extracted with chloroform
  7. additionthe extracts were treated with Darco
  8. customevaporated
  9. customdried in vacuo (50° C.)

Sources & evidence

ORD record
ord-85ebfd904c494d378fa23c059f531039
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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