Hydrochloric Acid → 2-Benzoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 617779ノート

反応式

HRID 617779 の反応式
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([C:12]([OH:14])=[O:13])[NH:3]1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>[OH-].[Na+]>[C:15]([N:3]1[CH:4]([C:12]([OH:14])=[O:13])[CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2]1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 27241351,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid hydrochloride

生成物 1

HCID 5700052-Benzoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

This compound was prepared according to Hein et. al., J. Amer. Chem. Soc.; 1962, 84, 4487-4494, incorporated by reference herein in its entirety. Thus, a slurry of 1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid hydrochloride (20.3 g, 95 mmol) in 2N NaOH (150 ml) was treated with benzoyl chloride (13.4 ml, 114 mmol) dropwise over 30 minutes. The mixture was stirred a further 1.5 hours, acidified to pH 2-3 (4N HCl), and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated to afford 16.4 g (61) of the title compound following recrystallization (acetone/water); MS: 280 m/z (M-H)-.

後処理

  1. customThis compound was prepared
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford
  8. custom16.4 g (61) of the title compound following recrystallization (acetone/water)

出典と根拠

ORDレコード
ord-b8b70703deac4ded93d5efb4e749d480
出典データセット
uspto-grants-1999_09
特許番号
US05952328

反応ノート

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