2-(2-(2-(Dipropylamino)ethyl)-6-nitrophenyl)acetic acid hydrochloride → Ropinirole Hydrochloride

HRID 1436863Notes

Reaction equation

HRID 1436863 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[C:6]=1[CH2:20][C:21]([OH:23])=O)([O-])=O>[Pd].CO>[CH3:16][CH2:15][CH2:14][N:13]([CH2:12][CH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]2[NH:2][C:21](=[O:23])[CH2:20][C:6]=12)[CH2:17][CH2:18][CH3:19].[ClH:1]

Participants

4

Reactant 1

HCID 135309012-(2-(2-(Dipropylamino)ethyl)-6-nitrophenyl)acetic acid hydrochloride

Product 1

HCID 68727Ropinirole Hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Nitro-6-[2-(N,N-Di-n-propyl amino)ethyl]phenyl acetic acid hydrochloride (100 g) is dissolved methanol (2000 ml) and then hydrogenated in presence of 10% Palladium on charcoal. The reaction mixture is filtered to obtain clear solution. Methanol is distilled out under vacuum at 50° C. Isopropanol (100 ml) is added to the residue and it is cooled, filtered and washed with isopropanol to obtain light yellow crystalline Ropinirole hydrochloride. The product is dried at 60-70° C. under vacuum. Yield 65-75 g.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto obtain clear solution
  3. distillationMethanol is distilled out under vacuum at 50° C
  4. additionIsopropanol (100 ml) is added to the residue and it
  5. temperatureis cooled
  6. filtrationfiltered
  7. washwashed with isopropanol

Sources & evidence

ORD record
ord-8d9d2df5078a400f9c7a920a129e80e1
Source dataset
uspto-grants-2009_11
Patent number
US07619095B2

Reaction notes

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