Methylamine → 4-Chloro-2-(2-methoxy-4-methylaminomethyl-phenoxy)-benzonitrile fumarate

HRID 1178468ノート

反応式

HRID 1178468 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]=O)=[CH:13][C:12]=2[O:19][CH3:20])[CH:3]=1.CN.[C:23]([BH3-])#[N:24].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>C(OCC)(=O)C.C(O)(=O)C.CO>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][NH:24][CH3:23])=[CH:13][C:12]=2[O:19][CH3:20])[CH:3]=1

参加物

7

反応物 4

HCID 6329MethylamineHCID 444972Fumaric AcidHCID 5003444Sodium cyanoborohydrideHCID 219303704-Chloro-2-(4-formyl-2-methoxy-phenoxy)-benzonitrile

生成物 1

HCID 219303444-Chloro-2-(2-methoxy-4-methylaminomethyl-phenoxy)-benzonitrile fumarate収率 80.1%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 10129899Acetic acid methanol溶媒

実験手順

4-Chloro-2-(4-formyl-2-methoxy-phenoxy)-benzonitrile (0.98 g, 3.4 mmol), methylamine (2M in methanol, 5.1 ml, 10.2 mmol) and sodium cyanoborohydride (0.24 g, 3.8 mmol) were stirred at ambient temperature in a 1% acetic acid/methanol solution (125 ml) for 20 h. The solvent was removed in vacuo. The residue was treated with 10% aqueous sodium carbonate and extracted with ethyl acetate. Fumaric acid (0.41 g, 3.5 mmol) was added to the separated ethyl acetate layer and the solvent removed in vacuo. The residue was triturated with ethyl acetate overnight, filtered and dried to give 4-chloro-2-(2-methoxy-4-methylaminomethyl-phenoxy)-benzonitrile fumarate (1.14 g, 80%) as a white solid.

後処理

  1. customThe solvent was removed in vacuo
  2. additionThe residue was treated with 10% aqueous sodium carbonate
  3. extractionextracted with ethyl acetate
  4. customthe solvent removed in vacuo
  5. customThe residue was triturated with ethyl acetate overnight
  6. filtrationfiltered
  7. customdried

出典と根拠

ORDレコード
ord-198da60d2a484167be39144ba74ac9da
出典データセット
uspto-grants-2007_10
特許番号
US07276528B2

反応ノート

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