Ammonium Chloride → 2-(2-Aminophenyl)-2-oxoethyl benzoate

HRID 358653Notes

Reaction equation

HRID 358653 reaction equation
[C:1]([O:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-])=O)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>O.[Fe]>[C:1]([O:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 536528172-(2-Nitrophenyl)-2-oxoethyl benzoate

Product 1

HCID 271530922-(2-Aminophenyl)-2-oxoethyl benzoate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-(2-nitrophenyl)-2-oxoethyl benzoate (50 g) and ammonium chloride (1 0.75 g) in water (800 ml) was stirred at 90° for 20 minutes. Iron powder (80 g) was added gradually over a period of 20 minutes. The mixture was stirred at 95° for a further 3 hours and filtered hot through diatomaceous earth (sold under the trade name CELITE). The filter bed was washed with hot (80° ) water (100 ml) and then separately with hot (60° ) ethyl acetate (5×300 ml). The aqueous filtrate and aqueous washing were combined and extracted with ethyl acetate (4×400 ml) and the extracts combined with the ethyl acetate washings from above, which had been washed with aqueous sodium chloride (6M, 200 ml). The combined ethyl acetate extracts were dried over sodium sulphate and evaporated to give the novel compound 2-(2-aminophenyl)-2-oxoethyl benzoate, m.p. 125°.

Workup

  1. stirringThe mixture was stirred at 95° for a further 3 hours
  2. filtrationfiltered hot through diatomaceous earth (
  3. washThe filter bed was washed with hot (80° ) water (100 ml)
  4. customseparately with hot (60° ) ethyl acetate (5×300 ml)
  5. washThe aqueous filtrate and aqueous washing
  6. extractionextracted with ethyl acetate (4×400 ml)
  7. washhad been washed with aqueous sodium chloride (6M, 200 ml)
  8. dry with materialThe combined ethyl acetate extracts were dried over sodium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-1839af924bae488fb913a6df2cd7e825
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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