Acetic Acid → HCID 67223522, compound

HRID 1947651Notes

Reaction equation

HRID 1947651 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[N:20]([CH:26]([CH3:28])[CH3:27])[C:19]2=[O:29].[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1.C(O)(=O)C>ClCCl>[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[C:21](=[O:25])[N:20]([CH:26]([CH3:27])[CH3:28])[C:19]3=[O:29])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22501979HCID 22501979, compound

Product 1

HCID 67223522HCID 67223522, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (1.03 g, 4.90 mmol) was added to a stirred solution of 5-amino-2-isopropyl-isoindole-1,3-dione (0.50 g, 2.69 mmol), 4-chlorobenzaldehyde (0.37 g, 2.69 mmol), and acetic acid (160 μl, 2.69 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 (5% methanol in dichloromethane) to afford the title compound as a light brown solid (160 mg, 20%). HPLC retention time 4.86 min. Mass spectrum (ES+) m/z 329 (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 (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-031be69cf4cd491e8da1ce2a317da65e
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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