Methylamine → HCID 10130977, compound

HRID 726150Notes

Reaction equation

HRID 726150 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5]/[C:6]/2=[CH:12]\[C:13](Cl)=[O:14].[CH3:16][NH2:17]>ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5]/[C:6]/2=[CH:12]\[C:13]([NH:17][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 11107593HCID 11107593, compound

Product 1

HCID 10130977HCID 10130977, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (E)-2-(4-chloro-6-fluoro-1-indanylidene)acetyl chloride (4.0 g, 0.015 mol) in dichloromethane (36 ml) was added dropwise to an ice-cold mixture of 40% aqueous methylamine (2.6 ml, 0.03mol) and dichloromethane (100 ml) and the mixture was stirred at ambient temperature for 18 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between 5% aqueous sodium bicarbonate and ethyl acetate. The ethyl acetate solution was dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel using ethyl acetate:hexanes (1:1) as eluent to give 1.59 g (44%) of (E)-2-(4-chloro-6-fluoro-1-indanylidene)-N-Methylacetamide as a white solid: mp 173°-175° C.; NMR (CDCl3): δ7.10-7.30 (m, 2H), 6.16 (s, 1H), 5.64 (br, 1H), 3.42-3.48 (m, 2H), 3.01-3.07 (m, 2H), 2.95 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between 5% aqueous sodium bicarbonate and ethyl acetate
  3. dry with materialThe ethyl acetate solution was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9adc8445ef6a47c8aeaaa3aa86178003
Source dataset
uspto-grants-1998_01
Patent number
US05708033

Reaction notes

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