2,4-Dimethoxyaniline → 224817-07-6

HRID 1007181Notes

Reaction equation

HRID 1007181 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:14]=1[NH2:15]>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([NH:15][C:14]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:13]=2[O:12][CH3:11])=[O:7])=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 176522,4-DimethoxyanilineHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 2713392224817-07-6Yield 59%

Procedure

The title compound was prepared from 6-chloronicotinoyl chloride and 2,4-dimethoxyaniline as described in Example 1. The reaction mixture was filtered to remove the precipitate and the filtrate was evaporated. The resulting solid was purified by CH2Cl2/hexane recrystallization to give a light purple solid in a yield of 59%. 1H NMR (DMSO-d6): 9.77 (s, 1H), 8.93 (s, 1H), 8.35-8.31 (m, 1H), 7.68 (d, J=7.8, 1H), 7.46 (d, J=9.0, 1H), 6.67 (d, J=2.4, 1H), 6.57-6.53 (m, 1H), 3.80 (s, 3H), 3.78 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the precipitate
  3. customthe filtrate was evaporated
  4. customThe resulting solid was purified by CH2Cl2/hexane recrystallization
  5. customto give a light purple solid in a yield of 59%

Sources & evidence

ORD record
ord-ea008885f5a6415ea509186c618a30d0
Source dataset
uspto-grants-2004_09
Patent number
US06794397B2

Reaction notes

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