Hydrochloric Acid → HCID 20551284, compound

HRID 1447289Notes

Reaction equation

HRID 1447289 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.C(=O)(O)[O-].[K+].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25].Cl>CN(C)C=O.O>[CH2:27]([O:26][C:24]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:6][CH:7]=1)=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformate2×HCID 516893Potassium Bicarbonate2×HCID 129189566-(4-Aminophenyl)-1,2-dihydro-2-oxonicotinic acid

Product 1

HCID 20551284HCID 20551284, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 6.9 g (30 mmol) of 6-(4-aminophenyl)-1,2-dihydro-2-oxonicotinic acid, 10 g (100 mmol) of potassium bicarbonate, and 100 ml of water is stirred at room temperature and 300 ml of dimethylformamide is added followed by 6.0 ml (43 mmol) of benzyl chloroformate. The mixture is stirred at room temperature for 2 hrs and 6.0 ml of benzyl chloroformate and 6.0 g of potassium bicarbonate are added. The reaction is stirred overnight at room temperature and poured into 700 ml of ice water. The pH is adjusted to 3 with hydrochloric acid and the precipitate is filtered, washed with water, and dried to give 9.44 g of 6-[4-(benzyloxycarbonylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid after recrystallization from N,N-dimethylacetamide-methanol.

Workup

  1. stirringThe mixture is stirred at room temperature for 2 hrs
  2. stirringThe reaction is stirred overnight at room temperature
  3. filtrationthe precipitate is filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-edced099ea3d420fa75f106c89e87003
Source dataset
uspto-grants-1982_02
Patent number
US04315858

Reaction notes

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