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

HRID 1242894

反応式

HRID 1242894 の反応式
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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 8028Tetrahydrofuran2 回HCID 219397344-[N-(4-Methoxybenzoyl)-N-methylamino]benzoic acid

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-dbdbb6ccd20c407f9823262629c5779a
出典データセット
uspto-grants-2006_10
特許番号
US07115750B1

関連ノート

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