Ammonia → 4-Bromo-5-aminophthalide

HRID 430466

Reaction equation

HRID 430466 reaction equation
[Br:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][O:5][C:6]2=[O:7].O.N>C(O)C.S([O-])([O-])(=O)=O.[Fe+2]>[Br:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][O:5][C:6]2=[O:7]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 185511854-Bromo-5-nitrophthalide

Product 1

HCID 185511684-Bromo-5-aminophthalideYield 70.3%

Reagents, catalysts & solvents 2

HCID 24393Ferrous SulfateCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

6.6 g of 4-bromo-5-nitrophthalide is dissolved in 45 ml of ethanol and added in drops to a mixture of 65 g of iron(II) sulfate, 220 ml of water and 65 ml of ammonia (33%) that is heated to 60° C. and thoroughly stirred. After 2 hours at 60° C., the mixture is absorptively precipitated five times with 200 ml of diethyl ether. The diethyl ether phases are concentrated by evaporation. As a residue, 4.1 g of 4-bromo-5-aminophthalide is obtained, flash point 176-180° C.

Workup

  1. customthe mixture is absorptively precipitated five times with 200 ml of diethyl ether
  2. concentrationThe diethyl ether phases are concentrated by evaporation

Sources & evidence

ORD record
ord-01241adb8b4647fabe5ad1922a7e6b1c
Source dataset
uspto-grants-2001_11
Patent number
US06323199B1

Linked notes

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