Hydrochloric Acid → 5-(N-formyl-N-methylamino-methyl)isatoic anhydride
Reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH:26]=[O:27])[CH3:25])=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].Cl>CN(C)C=O>[CH:26]([N:24]([CH2:23][C:20]1[CH:19]=[C:15]2[C:16]([O:18][C:1](=[O:2])[NH:13][C:14]2=[CH:22][CH:21]=1)=[O:17])[CH3:25])=[O:27]Participants
Procedure
There was suspended, in 15.2 mL of N,N-dimethylformamide, 3.82 g of 1,1′-carbonyl-diimidazole (CDI) and the resulting suspension was cooled to 5° C. To this slurry, there was added 4.0 g of 2-amino-5-(N-formyl-N-methylamino-methyl)benzoic acid in two portions, followed by the stirring of the same for one hour. After the confirmation of the disappearance of the starting material by HPLC, seed crystals were added to the slurry while dropwise adding 40.3 mL of a 1M hydrochloric acid aqueous solution to separate out solid and the resulting solid was isolated through filtration under reduced pressure. After washing the solid with 120 mL of water, it was dried at 70° C. for 13 hours under reduced pressure to thus give 3.20 g of the title compound as a white solid.
Workup
- additionAfter the confirmation of the disappearance of the starting material by HPLC, seed crystals were added to the slurry
- customto separate out solid
- customthe resulting solid was isolated through filtration under reduced pressure
- washAfter washing the solid with 120 mL of water, it
- dry with materialwas dried at 70° C. for 13 hours under reduced pressure to thus give 3.20 g of the title compound as a white solid
Sources & evidence
- ORD record
- ord-a21db31cc10842c1bee1ef073c323839
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08058432B2
Reaction notes
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