Hydrogen Bromide → 2-Amino-3',4'-dihydroxy-5'-nitroacetophenone hydrobromide

HRID 1781868Notes

Reaction equation

HRID 1781868 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[O:18]C=[N:16][C:15]=2C(OCC)=O)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9]C.[BrH:24]>>[BrH:24].[NH2:16][CH2:15][C:14]([C:5]1[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]([OH:9])=[C:3]([OH:2])[CH:4]=1)=[O:18]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 21459162Ethyl 5-(3,4-dimethoxy-5-nitrophenyl)-4-oxazolecarboxylate

Product 1

HCID 214589592-Amino-3',4'-dihydroxy-5'-nitroacetophenone hydrobromide

Procedure

1.0 g of ethyl 5-(3,4-dimethoxy-5-nitrophenyl)-4-oxazolecarboxylate is treated with 10 ml of constant-boiling hydrobromic acid and stirred at 140° for 2 hours. After distillation of the excess hydrobromic acid, the yellow residue is recrystallized from ethanol/acetone. There is obtained 2-amino-3',4'-dihydroxy-5'-nitroacetophenone hydrobromide in the form of yellow crystals of m.p. >250° (dec.).

Workup

  1. distillationAfter distillation of the excess hydrobromic acid
  2. customthe yellow residue is recrystallized from ethanol/acetone

Sources & evidence

ORD record
ord-b8fb12249774430bae0b862b8d550c7a
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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