Hydrochloric Acid → N-[4-(hydroxymethyl)phenyl]-4-methoxy-N-methylbenzamide

HRID 1242894

반응식

HRID 1242894 반응식
C1COCC1.B.[CH3:7][O:8][C:9]1[CH:27]=[CH:26][C:12]([C:13]([N:15]([C:17]2[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=2)[CH3:16])=[O:14])=[CH:11][CH:10]=1.Cl>O>[OH:22][CH2:21][C:20]1[CH:19]=[CH:18][C:17]([N:15]([CH3:16])[C:13](=[O:14])[C:12]2[CH:26]=[CH:27][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)=[CH:25][CH:24]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 8028Tetrahydrofuran2회HCID 219397344-[N-(4-Methoxybenzoyl)-N-methylamino]benzoic acid

생성물 1

HCID 21939995N-[4-(hydroxymethyl)phenyl]-4-methoxy-N-methylbenzamide수율 71%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

THF solution (1M, 16 ml) of borane was added dropwise to THF solution (10 ml) of 4-[N-(4-methoxybenzoyl)-N-methylamino]benzoic acid (1.14 g) under ice-cooling, which was stirred for 15 minutes, and then stirred at room temperature for 1 hour. After water was added to the reaction mixture, 1N hydrochloric acid was further added, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated sodium bicarbonate, and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using silica gel chromatography (development solvent; hexane˜hexane:ethyl acetate=1:2), and recrystallized (ethyl acetate-hexane) to give the titled compound (770 mg).

후처리

  1. temperaturecooling
  2. stirringstirred at room temperature for 1 hour
  3. additionwas further added
  4. extractionextraction
  5. washThe organic layer was washed with water and saturated sodium bicarbonate, and saturated aqueous sodium chloride solution
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified
  9. customrecrystallized (ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-dbdbb6ccd20c407f9823262629c5779a
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115750B1

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