Methylamine → HCID 20548484, compound

HRID 2058864Notes

Reaction equation

HRID 2058864 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9](=[O:14])[CH2:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19].CN>>[C:11]([C:10]1[C:9](=[O:14])[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[CH:19][N:18]([CH3:20])[CH:17]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 20548509HCID 20548509, compound

Product 1

HCID 20548484HCID 20548484, compound

Procedure

A 1.5 g. portion of 1-(3-fluorophenyl)-2,4-pentanedione was reacted with 15 ml. of N,N-dimethylformamide dimethyl acetal, and then with 10 ml. of 40% aqueous methylamine as described in Example 4. The reaction mixture was then evaporated under vacuum to dryness, and the crude product was chromatographed on a silica gel column with ethyl acetate to obtain 1 g. of the desired product, which was identified by nmr analysis in CDCl3, showing peaks at δ8.1-8.2 (m, 1H, pyridine); 6.9-7.6 (m, 5H, phenyl and 1 pyridine); 3.80 (s, 3H, N--CH3); 2.83 (s, 3H, COCH3).

Workup

  1. customThe reaction mixture was then evaporated under vacuum to dryness
  2. customthe crude product was chromatographed on a silica gel column with ethyl acetate
  3. customto obtain 1 g

Sources & evidence

ORD record
ord-fffe1f62765d4b39acb0aed41112ddef
Source dataset
uspto-grants-1982_03
Patent number
US04319916

Reaction notes

Loading…