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Hydrochloric Acid → 5-(N-formyl-N-methylamino-methyl)isatoic anhydride

HRID 1037818
Notes
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Reaction equation

HRID 1037818 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 580183122-amino-5-(N-formyl-N-methylamino-methyl)benzoic acid

Product 1

HCID 251343765-(N-formyl-N-methylamino-methyl)isatoic anhydride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. additionAfter the confirmation of the disappearance of the starting material by HPLC, seed crystals were added to the slurry
  2. customto separate out solid
  3. customthe resulting solid was isolated through filtration under reduced pressure
  4. washAfter washing the solid with 120 mL of water, it
  5. 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-6823eb923127454f87b2214ab18daea5
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08546610B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes