Acetic Acid → Methyl 4-(7-carbamoylnaphth-1-ylmethyl)-3-methoxybenzoate

HRID 2371813ノート

反応式

HRID 2371813 の反応式
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=2[O:24][CH3:25])=[CH:5][CH:4]=1)#[N:2].C(O)(=[O:28])C.B(F)(F)F.[OH-].[Na+]>C(Cl)Cl>[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=2[O:24][CH3:25])=[CH:5][CH:4]=1)(=[O:28])[NH2:2]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 6356Boron trifluorideHCID 14798Sodium HydroxideHCID 19906375Methyl 4-(7-cyanonaphth-1-ylmethyl)-3-methoxybenzoate

生成物 1

HCID 19906364Methyl 4-(7-carbamoylnaphth-1-ylmethyl)-3-methoxybenzoate収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
120 °C

実験手順

A mixture of methyl 4-(7-cyanonaphth-1-ylmethyl)-3-methoxybenzoate (394 mg), acetic acid (0.68 ml) and BF3 -etherate (0.22 ml) was heated to 120° C. for 15 min. After cooling, to the reaction mixture was added methylene chloride (50 ml) and 6N sodium hydroxide (3.5 ml) and it was stirred for 10 min. The aqueous layer was extracted with methylene chloride. The combined organic extract was washed (brine) and dried (MgSO4). Evaporation and trituration with hot ethyl acetate afforded methyl 4-(7-carbamoylnaphth-1-ylmethyl)-3-methoxybenzoate (262 mg, 63%) as a white solid; mp 215.0°-216.5° C.; MS(CI), m/e=350(M+H).

後処理

  1. temperatureAfter cooling, to the reaction mixture
  2. extractionThe aqueous layer was extracted with methylene chloride
  3. extractionThe combined organic extract
  4. washwas washed (brine)
  5. dry with materialdried (MgSO4)
  6. customEvaporation and trituration with hot ethyl acetate

出典と根拠

ORDレコード
ord-fb27b8402dce40adaa4c2c87f86cf071
出典データセット
uspto-grants-1992_03
特許番号
US05095038

反応ノート

読み込み中…