Ammonia → HCID 21867239, compound

HRID 857154Notes

Reaction equation

HRID 857154 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:5]=[C:6]([Br:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12](OC)=[C:11]([N+:17]([O-:19])=[O:18])[CH:10]=1.[NH3:26].O.Cl>COCCOCCO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:5]=[C:6]([Br:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:26])=[C:11]([N+:17]([O-:19])=[O:18])[CH:10]=1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 313Hydrochloric AcidHCID 962WaterHCID 70034269HCID 70034269, compound

Product 1

HCID 21867239HCID 21867239, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8134Diethylene Glycol Monomethyl EtherSolvent

Procedure

To methyl [3,5-dibromo-4-(4-methoxy-3-nitrophenoxy)phenyl]acetate (5 g), dissolved in 2-(2-methoxyethoxy)ethanol (50 mL) was added an aqueous solution of ammonia (32%, 7 mL). The reaction mixture was heated at 150° C. for, with continuos refill of ammonia. After 24 hours, water was added followed by an aqueous solution of hydrochloric acid. This was continued until the acidity of the solution reached pH 2. The aqueous phase was extracted with chloroform, washed with brine and dried over magnesium sulphate. After concentration of the organic phase, 4.1 g (84%) of methyl [3,5-dibromo-4-(4-amino-3-nitrophenoxy)phenyl]acetate was obtained as an yellow solid mass.

Workup

  1. extractionThe aqueous phase was extracted with chloroform
  2. washwashed with brine
  3. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-39f9381c21304bb9bda7b7aff209b4f2
Source dataset
uspto-grants-2006_12
Patent number
US07144909B2

Reaction notes

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