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

HRID 1957202Notes

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. 1 H-NMR (DMSO-d6): δ 3.8 (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-92474823efaf45bcb75370e8e3b17eb7
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05783575

Reaction notes

Loading…