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

HRID 280270Notes

Reaction equation

HRID 280270 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>C(O)C.[Pd]>[ClH:1].[CH2:14]([N:13]([CH2:17][CH2:18][CH3:19])[CH2:12][CH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]2[C:6]=1[CH2:20][C:21](=[O:23])[NH:2]2)[CH2:15][CH3:16]

Participants

4

Reactant 1

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

Product 1

HCID 68727Ropinirole HydrochlorideYield 77.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5.83 g (16.9 mmoles) of 2-nitro-6-(2-di-n-propylaminoethyl)-phenyl acetic acid hydrochloride and 0.6 g of 5% palladium-on-carbon in 250 cc of ethanol was hydrogenated at moderate pressure over 5.5 hours. The catalyst was filtered, washed with ethanol, and the filtrate evaporated to dryness in vacuo. The white residue was crystallized from 550 cc of hot acetonitrile to give 3.89 g of 4-(2-di-n-propylaminoethyl)-2(3H)-indolone hydrochloride, mp 240°-2°.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with ethanol
  3. customthe filtrate evaporated to dryness in vacuo
  4. customThe white residue was crystallized from 550 cc of hot acetonitrile

Sources & evidence

ORD record
ord-28ef0f20666342f1a955a04f86f494f5
Source dataset
uspto-grants-1986_05
Patent number
US04588740

Reaction notes

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