Dimethylformamide → 1-Methyl-2,4,6-trichloroindole-3-carbaldehyde

HRID 1735098Notes

Reaction equation

O=P(Cl)(Cl)[Cl:3].[CH3:6][N:7]1[C:15]2[C:10](=[C:11]([Cl:17])[CH:12]=[C:13]([Cl:16])[CH:14]=2)[CH2:9][C:8]1=O.CN([CH:22]=[O:23])C>>[CH3:6][N:7]1[C:15]2[C:10](=[C:11]([Cl:17])[CH:12]=[C:13]([Cl:16])[CH:14]=2)[C:9]([CH:22]=[O:23])=[C:8]1[Cl:3]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24813Phosphorus oxychloride

HCID 190689871-Methyl-4,6-dichloro-1,3-dihydroindol-2-one

Product 1

HCID 190689781-Methyl-2,4,6-trichloroindole-3-carbaldehyde

Procedure

Prepared from POCl3 (11 ml), DMF (11 ml), (43) (8.4 g), yielding (48) 6.5 g as crude product sufficiently pure for the next synthesis. 1H-NMR (DMSO-d6): δ3.8 (s, 3H), 7.43 (d, 1H), 7.86 (d, 1H), 10.52 (s, 1H). In this reaction the reaction time was 24 h instead of 3 h.

Sources & evidence

ORD record: ord-fb75c43ee94d4565b54e03135b4a3711
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05536721

Reaction notes

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