Acetic Acid → HCID 67223633, compound

HRID 1947633Notes

Reaction equation

HRID 1947633 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][NH:22][C:23]2=[O:26])=[CH:18][CH:17]=1.Cl[C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1.C(O)(=O)C>ClCCl>[CH2:32]([NH:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][NH:22][C:23]2=[O:26])=[CH:18][CH:17]=1)[C:31]1[CH:34]=[CH:35][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 131528447-Amino-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 67223633HCID 67223633, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (1.29 g, 6.16 mmol) was added to a stirred solution of 7-amino-3,4-dihydro-2H-isoquinolin-1-one (500 mg, 3.08 mmol), 4-chlorobenzaldehyde (431 mg, 3.08 mmol) and acetic acid (183 μl, 3.08 mmol) in anhydrous dichloromethane (25 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 (50% ethyl acetate in dichloromethane) to yield the title compound as a pale yellow solid (287 mg, 16%). HPLC retention time 4.09 min. Mass spectrum (ES+) m/z 287 (M+H).

Workup

  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 (50% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-aea609a8fa094890a9e3fe951d427954
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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