Acetic Acid → HCID 67224204, 화합물

HRID 1947647노트

반응식

HRID 1947647 반응식
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([CH3:28])([CH3:27])[CH2:21][NH:22][C:23]2=[O:26])=[CH:18][CH:17]=1.[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1.C(O)(=O)C>ClCCl>[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([CH3:28])([CH3:27])[CH2:21][NH:22][C:23]3=[O:26])=[CH:18][CH:17]=2)=[CH:32][CH:31]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 219596427-Amino-4,4-dimethyl-3,4-dihydroisoquinolin-1(2h)-one

생성물 1

HCID 67224204HCID 67224204, 화합물수율 39%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Sodium triacetoxyborohydride (800 mg, 3.79 mmol) was added to a stirred solution of 7-amino-4,4-dimethyl-3,4-dihydro-2H-isoquinolin-1-one (220 mg, 1.15 mmol), 4-chlorobenzaldehyde (324 mg, 2.31 mmol) and acetic acid (69 μl, 1.15 mmol) in anhydrous dichloromethane (10 ml) at room temperature. The reaction was stirred overnight and quenched with the addition of water. The organic phase was separated, washed with brine, then dried (MgSO4) and evaporated in vacuo. The resulting residue was purified by flash column chromatography (20% ethyl acetate in dichloromethane) to afford the title compound as a light brown solid (140 mg, 39%). HPLC retention time 4.40 min. Mass spectrum (ES+) m/z 315 (M+H).

후처리

  1. customquenched with the addition of water
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe resulting residue was purified by flash column chromatography (20% ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-add29f979b4b4f1abadcb8bd616fec3a
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399481B2

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