Pyrrolidine → HCID 59133095, compound

HRID 1993243Notes

Reaction equation

HRID 1993243 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[CH3:13].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18].N1CC[CH2:24][CH2:23]1>CN(C=O)C>[Br:1][C:2]1[C:3](/[CH:13]=[CH:19]/[N:17]2[CH2:16][CH2:24][CH2:23][CH2:18]2)=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 113570121-Bromo-4-methoxy-2-methyl-3-nitrobenzene

Product 1

HCID 59133095HCID 59133095, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1-bromo-4-methoxy-2-methyl-3-nitrobenzene (1.400 g, 5.68 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (0.884 mL, 6.657 mmol) in DMF (10.0 mL) was added pyrrolidine (0.555 mL, 6.656 mmol) and the mixture was heated to at 110° C. for 4 h. The DMF was removed and the residue was recrystallized from DCM:methanol (1:6) mixture to afford 1-[(E)-2-(6-bromo-3-methoxy-2-nitrophenyl)vinyl]pyrrolidine.

Workup

  1. customThe DMF was removed
  2. customthe residue was recrystallized from DCM:methanol (1:6) mixture

Sources & evidence

ORD record
ord-649bb96dbbaa4ea6a1520aa06b7284d6
Source dataset
uspto-grants-2010_01
Patent number
US07651687B2

Reaction notes

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