Hydrochloric Acid → 2-Carbamoyl-6-nitrobenzoic Acid

HRID 535782

Reaction equation

HRID 535782 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:14])[NH:7][C:8]2=[O:13])([O-:3])=[O:2].[OH-:15].[Na+].Cl>O>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([C:8]([NH2:7])=[O:13])[C:5]=1[C:6]([OH:14])=[O:15])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 117793-NitrophthalimideHCID 14798Sodium Hydroxide

Product 1

HCID 45927482-Carbamoyl-6-nitrobenzoic AcidYield 96.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

Commercially available 4-nitro-isoindole-1,3-dione (1) (25 g, 0.13 mol) was stirred in water (300 mL) at 0° C. Over a few minutes, an aqueous solution of sodium hydroxide (30% w/w, 35 g, 0.26 mol) was added. The mixture was stirred for 1.5 h at 0-5° C. The cold solution was acidified with concentrated HCl (22 mL, 0.26 mol) and the product precipitated as a white solid. After allowing to stand overnight in a refrigerator, the mixture was filtered to afford the title compound (26.3 g, 96%) as a white solid: 1H NMR (300 MHz, DMSO) δ 8.2 (s, 1H), 8.15 (d, 1H), 7.93 (d, 1H), 7.88-7.65 (m, 2H); ESIMS m/z 211 ([M+H]+), m/z 209 ([M−H]−).

Workup

  1. waitOver a few minutes
  2. customthe product precipitated as a white solid
  3. waitto stand overnight in a refrigerator
  4. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-a4e44332efb34e9ba8bf529f0a480742
Source dataset
uspto-grants-2014_10
Patent number
US08859558B2

Linked notes

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