Dimethylformamide → HCID 178526062, compound

HRID 1389399Notes

Reaction equation

HRID 1389399 reaction equation
CN(C)C=O.[OH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[N:10]=[CH:9][C:8]=1[C:17]([OH:19])=[O:18].O[N:21]1[C:25](=[O:26])[CH2:24][CH2:23][C:22]1=[O:27].S(Cl)(Cl)=O>N1C=CC=CC=1>[OH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[N:10]=[CH:9][C:8]=1[C:17]([O:19][N:21]1[C:25](=[O:26])[CH2:24][CH2:23][C:22]1=[O:27])=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 80170N-HydroxysuccinimideHCID 178524722HCID 178524722, compound

Product 1

HCID 178526062HCID 178526062, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of dimethylformamide (47.5 kg) containing pyridine (4.7 kg), there were added 4-hydroxy-1,5-naphthyridine-3-carboxylic acid (2.8 kg) and N-hydroxy-succinimide (2.2 kg). To the mixture, there was dropwise added thionyl chloride (2.1 kg) while stirring at room temperature, and stirring was continued for 5 hours at the same temperature. The precipitated crystals were collected by filtration, washed with acetone and dried under reduced pressure to give 4.3 kg of N-(4-hydroxy-1,5-naphthyridine-3-carbonyloxy)succinimide. Purity, 97%

Workup

  1. stirringstirring
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with acetone
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-94fa9163ef924f268654c835b6f89bcd
Source dataset
uspto-grants-1981_01
Patent number
US04244870

Reaction notes

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