Sodium Hydroxide → 3,8-Dimethyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid

HRID 1920738

반응식

HRID 1920738 반응식
C([O:3][C:4]([C:6]1[C:15]2[C:10](=[C:11]([CH3:16])[CH:12]=[CH:13][CH:14]=2)[C:9](=[O:17])[N:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]=1[CH3:24])=[O:5])C.[OH-].[Na+]>CS(C)=O.O>[CH3:24][C:7]1[N:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9](=[O:17])[C:10]2[C:15]([C:6]=1[C:4]([OH:5])=[O:3])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 577333143,8-Dimethyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid ethyl ester

생성물 1

HCID 577334143,8-Dimethyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid수율 41.2%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

A solution of 3,8-dimethyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid ethyl ester (200 mg, 0.62 mmol) in DMSO (3 ml) and aqueous 1N NaOH (2 ml, 2 mmol) was heated under microwave irradiation at +120° C. for 20 min and diluted with water (30 ml). Uncharged impurities were extracted with diethyl ether (30 ml) and the aqueous solution was poured into ice (50 g) with aqueous 2M HCl (10 ml). The obtained precipitate was filtered, washed with water and dried in vacuo to give 75 mg of yellow solid. Yield 41%. LC-MS (m/z) 293.9 (MH+); tR=1.09. 1H NMR (500 MHz, DMSO-d6): 1.95 (s, 3H), 2.74 (s, 3H), 7.3 (d, 1H), 7.32 (d, 2H), 7.48 (two overlapping m, 2H), 7.55 (t, 2H), 7.62 (t, 1H), 13.42 (b, 1H).

후처리

  1. extractionwere extracted with diethyl ether (30 ml)
  2. additionthe aqueous solution was poured into ice (50 g) with aqueous 2M HCl (10 ml)
  3. filtrationThe obtained precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-549ef66e534a4790bc3c0a51b41ae6ad
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173639B2

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