Acetic Acid → HCID 67224314, compound

HRID 1947643Notes

Reaction equation

HRID 1947643 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]([C:20]([CH3:30])([CH3:29])[CH2:21][N:22]([CH2:27][CH3:28])[C:23]2=[O:26])=[CH:18][CH:17]=1.[Cl:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1.C(O)(=O)C>ClCCl>[Cl:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([CH3:29])([CH3:30])[CH2:21][N:22]([CH2:27][CH3:28])[C:23]3=[O:26])=[CH:18][CH:17]=2)=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67223501HCID 67223501, compound

Product 1

HCID 67224314HCID 67224314, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (77 mg, 0.36 mmol) was added to a stirred solution of 7-amino-2-ethyl-4,4-dimethyl-3,4-dihydro-2H-isoquinolin-1-one (40 mg, 0.18 mmol), 4-chlorobenzaldehyde (31 mg, 0.22 mmol) and acetic acid (11 μl, 0.18 mmol) in anhydrous dichloromethane (6 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 preparative tlc (20% ethyl acetate in petroleum ether) to afford the title compound as a colourless solid (20 mg, 32%). HPLC retention time 4.78 min. Mass spectrum (ES+) m/z 343 (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 preparative tlc (20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-44907ae80bf14f18a445ef4ec741c468
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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