Sodium Hydroxide → 3,4-Dimethoxybenzylidene-1-methylpyrrolidine

HRID 1278035Notes

Reaction equation

HRID 1278035 reaction equation
COC([C:5](=[C:16]1[CH2:20][CH2:19][CH2:18][N:17]1[CH3:21])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)=O.[OH-].[Na+]>Cl>[CH3:15][O:14][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[O:12][CH3:13])[CH:5]=[C:16]1[CH2:20][CH2:19][CH2:18][N:17]1[CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54493431HCID 54493431, compound

Product 1

HCID 544128563,4-Dimethoxybenzylidene-1-methylpyrrolidine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Boil 12.4 g of 2-(α-methoxycarbonyl-3,4-dimethoxybenzylidene)-1-methylpyrrolidine for 15 minutes with 40 ml of conc. hydrochloric acid. Cool the resulting reaction mixture before rendering it alkaline with sodium hydroxide solution. Filter off the thus-produced precipitate and recrystallize it from ethanol/water 2:1 to obtain 3.2 g (32% of theory) of title compound having a m.p. of 72°.

Workup

  1. temperatureCool
  2. customthe resulting reaction mixture
  3. filtrationFilter off the thus-produced precipitate
  4. customrecrystallize it from ethanol/water 2:1

Sources & evidence

ORD record
ord-2b51e41249e7434ba744ad23f3e32ed5
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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