Hydrochloric Acid → Benzoic acid, 4-amino-3-nitro-, ethyl ester

HRID 1660795Notes

Reaction equation

HRID 1660795 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].Cl.[CH2:15](O)[CH3:16]>CCOCC>[CH2:15]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([NH2:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1)[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 74115Benzoic acid, 4-amino-3-nitro-

Product 1

HCID 3018687Benzoic acid, 4-amino-3-nitro-, ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Amino-3-nitrobenzoic acid (5.0 g, 27.4 mmol) was dissolved in ethanol (100 mL) and treated with a 2N solution of HCl in ether (30 mL). The reaction mixture was refluxed for 16 h, then the solvent was removed in vacuo. The crude compound was dissolved in dichloromethane and washed with NaOH 0.5N. The organic phase was dried over sodium sulfate and the solvent was removed. 4-Amino-3-nitrobenzoic acid ethyl ester was thus obtained as a yellow solid, 4.6 g, (79%), MS (ISP): m/e=211.1 (M+H+.), and used crude in the following reaction.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. customthe solvent was removed in vacuo
  3. dissolutionThe crude compound was dissolved in dichloromethane
  4. washwashed with NaOH 0.5N
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-b83e5d9ca64245829231f6e65aacbacf
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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