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

HRID 2371813노트

반응식

HRID 2371813 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fb27b8402dce40adaa4c2c87f86cf071
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05095038

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