Hydrochloric Acid → HCID 13935996, compound

HRID 649532Notes

Reaction equation

HRID 649532 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[O:12])[CH2:8][C:7](=O)[C:6]=2[CH:23]=1.[C-]#N.[K+].[C:27](=[O:30])([O-])[O-].[NH4+:31].[NH4+:32].Cl.[CH2:34]([OH:36])C>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[O:12])[CH2:8][C:7]3([C:34](=[O:36])[NH:32][C:27](=[O:30])[NH:31]3)[C:6]=2[CH:23]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 16766929HCID 16766929, compound

Product 1

HCID 13935996HCID 13935996, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-fluoro-3,4-dihydro-N-(4-methoxyphenyl)-4-oxo-2H-1-benzopyran-2-carboxamide (220 mg, 0.7 mmol), potassium cyanide (97.5 mg, 1.5 mmol) and ammonium carbonate (400 mg, 4.2 mmol) in 2.1 ml of 60% aqueous ethanol was heated at 65° to 70° C. in a sealed tube for 40 hours. The reaction mixture was diluted with 5.0 ml of water and then acidified with 6N-hydrochloride acid to pH 1. The formed precipitate was filtered and recrystallized from ethanol to give 67.3 mg (25.0%) of the desired compound.

Workup

  1. temperaturewas heated at 65° to 70° C. in a sealed tube for 40 hours
  2. filtrationThe formed precipitate was filtered
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-41b11495956648f790d089a9a19ed8bc
Source dataset
uspto-grants-1988_04
Patent number
US04740517

Reaction notes

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