Hydrochloric Acid → 2-(4-Amino-3-nitrobenzoyl)benzoic acid

HRID 2367080Notes

Reaction equation

HRID 2367080 reaction equation
Cl[C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].Cl.[OH-].[NH4+:24]>>[NH2:24][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 665622-(4-Chloro-3-nitrobenzoyl)benzoic acid

Product 1

HCID 27975222-(4-Amino-3-nitrobenzoyl)benzoic acidYield 98%

Procedure

A solution of 2-(4-chloro-3-nitrobenzoyl)benzoic acid (5.0 g, 16.36 mmol) was heated to reflux in 28-30% aq. ammonium hydroxide (100 mL) for 18 h. The solution was cooled to room temperature followed by addition of 6N aq. hydrochloric acid until pH to 7. The precipitated yellow solid was collected by filtration and washed with water then dried in vacuo to provide 2-[(4-amino-3-nitrophenyl)carbonyl]benzoic acid (4.60 g, 98%). MS (EI) for C14H10N2O5: 288 (MH+).

Workup

  1. filtrationThe precipitated yellow solid was collected by filtration
  2. washwashed with water
  3. customthen dried in vacuo

Sources & evidence

ORD record
ord-3af1147cd0704a9683252867da7e1433
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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