Dimethylformamide → 5-methyl-4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehyde

HRID 991792Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2=[CH:8][NH:9][CH:10]=[C:4]2[C:3]1=[O:11].CN([CH:15]=[O:16])C.O=P(Cl)(Cl)Cl>>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2=[C:8]([CH:15]=[O:16])[NH:9][CH:10]=[C:4]2[C:3]1=[O:11]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24813Phosphorus oxychloride

HCID 98988745-Methyl-6,7-dihydro-2H-pyrrolo[3,4-c]pyridin-4(5H)-one

Product 1

HCID 99205265-methyl-4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehydeYield 33%

Procedure

5-Methyl-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one was formylated under standard Vilsmeier conditions using DMF (3 equiv.) and POCl3 (1.1 equiv.) to give 250 mg (33%) of 5-methyl-4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehyde.

Sources & evidence

ORD record: ord-ecbcf408e6fc434992d13099fba0a7e9
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06465507B2

Reaction notes

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