Ammonia → 2-(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)acetamide

HRID 639196ノート

反応式

HRID 639196 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:8]=2)[C:3]=1[CH2:16][C:17]([OH:19])=O.[NH3:20]>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:8]=2)[C:3]=1[CH2:16][C:17]([NH2:20])=[O:19]

参加物

4

反応物 2

HCID 222AmmoniaHCID 68706916(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-acetic acid

生成物 1

HCID 687039782-(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)acetamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-acetic acid (276 mg, 0.99 mmol) is dissolved under an atmosphere of argon in DMF (3 ml). 1,1-Carbonyl diimidazole (177 mg, 1.09 mmol) is added, and the clear solution is stirred at RT for 3 h. A conc. aqueous solution of ammonia (25%, 6 ml) is added, and stirring is continued for 10 minutes at RT. TLC analysis indicates complete consumption of starting material. The reaction mixture is poured on water. The aqueous layer is extracted with EtOAc, which is then washed with brine and dried over Na2SO4. After removal of solvent, the residue is found to be pure title compound, with no need of purification. 1H NMR (d6-DMSO, 400 MHz): δ 2.18 (s, 6H), 3.53 (s, 2H), 4.08 (s, 2H), 6.96-7.08 (br, 2H), 7.48-7.68 (m, 2H), 7.78-7.86 (m, 2H), 7.96-8.00 (d, J=10 Hz, 1H). ES+-MS: 277.3, 279.2 [M+H]+.

後処理

  1. stirringstirring
  2. waitis continued for 10 minutes at RT
  3. customconsumption of starting material
  4. additionThe reaction mixture is poured on water
  5. extractionThe aqueous layer is extracted with EtOAc, which
  6. washis then washed with brine
  7. dry with materialdried over Na2SO4
  8. customAfter removal of solvent
  9. customwith no need of purification

出典と根拠

ORDレコード
ord-8714d1cfa9e54d509650bdbceb4f0110
出典データセット
uspto-grants-2010_04
特許番号
US07691861B2

反応ノート

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