Sodium hydride → HCID 58980801, compound

HRID 1181373Notes

Reaction equation

HRID 1181373 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][OH:8].[H-].[Na+].Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[O:21][CH3:22]>CN(C=O)C>[CH3:22][O:21][C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[O:8][CH2:7][C@@H:3]1[CH2:4][CH2:5][CH2:6][N:2]1[CH3:1]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 705192-Chloro-5-nitroanisoleHCID 643492(2S)-1-Methyl-2-pyrrolidinemethanol

Product 1

HCID 58980801HCID 58980801, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of [(2S)-1-methylpyrrolidin-2-yl]methanol (11.5 g, 0.10 mol), DMF (150 mL) and NaH (4.0 g, 60% in mineral oil, 0.1 mol) was agitated for 30 minutes under an atmosphere of nitrogen. A DMF (100 mL) solution of 1-chloro-2-methoxy-4-nitrobenzene (18.7 g, 0.10 mol) was added and the mixture agitated overnight at RT. The mixture was concentrated, diluted with ethyl acetate, extracted three times with water, dried, filtered, then concentrated to give the product as a tan oil (16.78 g, 63%). LCMS m/z 267 (MH+). 1H NMR (300 MHz, DMSO-d6) δ 7.88 (d, 1H), 7.73 (s, 1H), 7.19 (d, 1H), 4.06 (m, 2H), 3.88 (s, 3H), 2.80 (m, 1H), 2.60 (m, 1H), 2.36 (s, 3H), 2.20 (m, 1H). 1.90 (m, 1H), 1.67 (m, 3H) ppm.

Workup

  1. stirringthe mixture agitated overnight at RT
  2. concentrationThe mixture was concentrated
  3. additiondiluted with ethyl acetate
  4. extractionextracted three times with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-53f1251dff8744779fb0271ae9ab9270
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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