4-Nitrophthalimide → 1,2-Benzenedicarboxamide, 4-nitro-

HRID 1730618

Reaction equation

HRID 1730618 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[NH:10][C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[OH-].[NH4+:16]>O>[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([NH2:10])=[O:12])[C:7](=[CH:13][CH:14]=1)[C:8]([NH2:16])=[O:9])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 69694-NitrophthalimideHCID 14923Ammonium Hydroxide

Product 1

HCID 831671,2-Benzenedicarboxamide, 4-nitro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Commercial 4-nitrophthalimide (500 g; 2.60 moles; mp 196°-200° C) is added quickly to a stirred solution of 15.6 N ammonium hydroxide (3500 ml). With continued stirring, external heating (water bath, 45° C) is applied until frothing ceases (1 hour). The resulting precipitate is collected, washed with ice water (2 × 400ml) then recrystallized with acetone (2 × 400 ml) and dried to yield 440 g of I as pale yellow crystals; yield, 81%, mp 200°-202° C; lit (6) mp 200° C.

Workup

  1. customis applied until frothing ceases (1 hour)
  2. customThe resulting precipitate is collected
  3. washwashed with ice water (2 × 400ml)
  4. customthen recrystallized with acetone (2 × 400 ml)
  5. customdried
  6. customto yield 440 g of I as pale yellow crystals
  7. customyield

Sources & evidence

ORD record
ord-e2234f2e013146d0b5c47c540d771137
Source dataset
uspto-grants-1976_11
Patent number
US03993631

Linked notes

Loading…