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Dimethylformamide → 2-Chloro-5-methoxy-1-phenyl-1h-indole-3-carbaldehyde

HRID 1510079
Notes
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Reaction equation

HRID 1510079 reaction equation
CN(C=O)C.[CH2:6]([Cl:8])Cl.P(Cl)(Cl)(Cl)=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:20](=[O:31])[CH2:19]2>C(Cl)(Cl)Cl.N1C=CC=CC=1.CC(=O)OCC>[Cl:8][C:6]1[N:21]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:22]2[C:18]([C:19]=1[CH:20]=[O:31])=[CH:17][C:16]([O:15][CH3:14])=[CH:24][CH:23]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 136034182h-Indol-2-one,1,3-dihydro-5-methoxy-1-phenyl-

Product 1

HCID 872052842-Chloro-5-methoxy-1-phenyl-1h-indole-3-carbaldehyde

Reagents, catalysts & solvents 3

HCID 1049
Pyridine
Solvent
HCID 6212ChloroformSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A solution of DMF (2.3 ml) and DCM (2.3 ml) under argon was cooled to 0° C. With stirring, phosphorus oxychloride (2.14 ml, 22.9 mmol) was added within 15 min, and the mixture was stirred for further 30 min at 0° C. Then the compound of step 2 (557 mg, 2.33 mmol), dissolved in chloroform (5.77 ml) and pyridine (1.15 ml), was added to the cooled solution. The reaction mixture was stirred at room temperature overnight. The mixture was slowly poured into 300 ml of ice and after a few minutes EA was added. The organic layer was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. Column chromatography of the residue on silica gel (EA/HEP 1:8) yielded 456 mg of the title compound as a white solid.

Workup

  1. stirringthe mixture was stirred for further 30 min at 0° C
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. additionwas added
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-83d74cc4b65541d9a060479d76a0a81f
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08211885B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes