Ethanol → Ethyl 4-amino-2-nitrobenzoate

HRID 265450Notes

Reaction equation

HRID 265450 reaction equation
C([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)(=O)C.[CH2:17](O)[CH3:18]>Cl>[CH2:17]([O:11][C:9](=[O:10])[C:8]1[CH:12]=[CH:13][C:5]([NH2:4])=[CH:6][C:7]=1[N+:14]([O-:16])=[O:15])[CH3:18]

Participants

4

Reactant 2

HCID 702EthanolHCID 731384-(Acetylamino)-2-nitrobenzoic acid

Product 1

HCID 22832069Ethyl 4-amino-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-acetylamino-2-nitrobenzoic acid (1.80 g, 8.0 mmol) in 12N hydrochloric acid (14 mL) and absolute ethyl alcohol (10 mL) was heated to 90°-100° C. for 5 h. Concentrated down in vacuo to remove ethyl alcohol only, adjusted pH to 4 with 1N sodium hydroxide and filtered off precipitate to give 140 mg (Y: 8%) of the title compound; 1H-NMR (CDCl3): δ 7.61 (d, J=8.5 Hz, 1H), 6.82 (d, J=2.1 Hz, 1H), 6.74 (dd, J=8.5, 2.1 Hz, 1H), 6.52 (bs, 2H), 4.17 (q, J=7.1 Hz, 2H), 1.21 (t, J=7.1 Hz, 3H); MS (DCI) m/e: 211 (MH+).

Workup

  1. concentrationConcentrated down in vacuo
  2. customto remove ethyl alcohol only
  3. filtrationfiltered off precipitate

Sources & evidence

ORD record
ord-3825c717144b476c9075384455df7fe0
Source dataset
uspto-grants-1997_07
Patent number
US05648385

Reaction notes

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