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Acetic Acid → HCID 67223272, compound

HRID 1947631
Notes
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Reaction equation

HRID 1947631 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]([CH2:26][CH3:27])[CH2:19]2.[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=1.C(O)(=O)C>C(#N)C>[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[C:21](=[O:25])[N:20]([CH2:26][CH3:27])[CH2:19]3)=[CH:31][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 529112495-Amino-2-ethyl-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 67223272HCID 67223272, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

Sodium triacetoxyborohydride (1.28 g, 6.10 mmol) was added to a stirred solution of 5-amino-2-ethyl-2,3-dihydro-isoindol-1-one (540 mg, 3.05 mmol), 4-chlorobenzaldehyde (854 mg, 6.10 mmol) and acetic acid (183 μl, 3.05 mmol) in anhydrous acetonitrile (12 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 (0 to 20% ethyl acetate in dichloromethane) to yield the title compound as a light brown solid (148 mg, 16%). HPLC retention time 4.23 min. Mass spectrum (ES+) m/z 301 (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 (0 to 20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-62d4f66aa6844cf7850049d1186b323c
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399481B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes