Methylamine → 4-Chloro-2-[2-ethoxy-3-(methylaminomethyl)phenoxy]benzonitrile fumarate

HRID 1178476ノート

反応式

HRID 1178476 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][CH:14]=[C:13]([CH:17]=O)[C:12]=2[O:19][CH2:20][CH3:21])[CH:3]=1.CN.[C:24]([BH3-])#[N:25].[Na+].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>C(OCC)(=O)C.C(O)(=O)C.CO>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[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][CH:14]=[C:13]([CH2:17][NH:25][CH3:24])[C:12]=2[O:19][CH2:20][CH3:21])[CH:3]=1

参加物

7

反応物 4

HCID 6329MethylamineHCID 444972Fumaric AcidHCID 5003444Sodium cyanoborohydrideHCID 219303824-Chloro-2-(2-ethoxy-3-formylphenoxy)benzonitrile

生成物 1

HCID 219303734-Chloro-2-[2-ethoxy-3-(methylaminomethyl)phenoxy]benzonitrile fumarate収率 67.6%

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-(2-ethoxy-3-formylphenoxy)benzonitrile (0.55 g, 1.8 mmol), methylamine (2M in methanol, 3.0 mL, 6.0 mmol) and sodium cyanoborohydride (0.13 g, 2.1 mmol) were stirred at ambient temperature in a 1% acetic acid/methanol solution (55 mL) for 3 days. The solvent was removed in vacuo. The residue was treated with 10% sodium carbonate solution and extracted with ethyl acetate. Fumaric acid (0.21 g, 1.8 mmol) was added to the separated ethyl acetate layer and the solvent removed in vacuo. The residue was triturated overnight with ethyl acetate, collected by filtration, and dried to give 4-chloro-2-[2-ethoxy-3-(methylaminomethyl)phenoxy]benzonitrile fumarate (527 mg, 67%) as a white solid.

後処理

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

出典と根拠

ORDレコード
ord-648a42af66064baf852cde67161219c2
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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