Hydrogen Bromide → 7-Hydroxy Ropinirole HBr

HRID 1446966Notes

Reaction equation

HRID 1446966 reaction equation
[BrH:1].[CH2:2]([N:5]([CH2:20][CH2:21][CH3:22])[CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:14]([O:17]C)=[C:13]2[C:9]=1[CH2:10][C:11](=[O:19])[NH:12]2)[CH2:3][CH3:4].Br>>[BrH:1].[CH2:20]([N:5]([CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]2[C:9]=1[CH2:10][C:11](=[O:19])[NH:12]2)[CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 12807549HCID 12807549, compound

Product 1

HCID 128075517-Hydroxy Ropinirole HBrYield 75%

Procedure

A 0.284 g (0.765 mmole) portion of 4-(2-di-n-propylaminoethyl)-7-methoxy-2(3H)-indolone hydrobromide was placed in a flask and approximately 5 ml of constant boiling hydrobromic acid was distilled (from stannous chloride) directly into the flask. The resulting mixture was stirred at reflux under an argon atmosphere for 3 hours. Evaporation of the solvents produced a solid residue which was recrystallized twice from methanol-ethyl acetate to provide 0.206 g (75%) of 4-(2-di-n-propylaminoethyl)-7-hydroxy-2(3H)-indolone hydrobromide. m.p. 252°-254°.

Workup

  1. distillationwas distilled (from stannous chloride) directly into the flask
  2. temperatureat reflux under an argon atmosphere for 3 hours
  3. customEvaporation of the solvents
  4. customproduced a solid residue which
  5. customwas recrystallized twice from methanol-ethyl acetate

Sources & evidence

ORD record
ord-9ed2bdb6b0454daf92a14e3cbff9cb53
Source dataset
uspto-grants-1982_02
Patent number
US04314944

Reaction notes

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