Dimethylformamide → HCID 19104591, compound

HRID 1197739Notes

Reaction equation

HRID 1197739 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[CH2:17][OH:18].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[OH:18][CH2:17][CH:13]1[CH2:14][CH2:15][CH2:16][N:12]1[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 90908ProlinolHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 19104591HCID 19104591, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

20 g of 5-fluoro-2-nitrotoluene, 14.3 g of 2-pyrrolidine methanol and 20 g of potassium carbonate were added to 100 ml of dimethylformamide. They were stirred at 100° C. for 2 h. After leaving to cool, the reaction mixture was poured into water. After extraction with ethyl acetate, the extract was washed with water, concentrated and recrystallized from acetonitrile to obtain 26 g of 2-hydroxymethyl-N-(3-methyl-4-nitrophenyl)pyrrolidine (d) as yellow crystals.

Workup

  1. customAfter leaving
  2. temperatureto cool
  3. extractionAfter extraction with ethyl acetate
  4. washthe extract was washed with water
  5. concentrationconcentrated
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-5ea683e842f041ea999a776089518de2
Source dataset
uspto-grants-1994_01
Patent number
US05278034

Reaction notes

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