Hydrochloric Acid → 5-Amino-2-(4-amino-3-fluorophenyl)-6,8-difluoro-4H-1-benzopyran-4-one

HRID 1736107Notes

Reaction equation

HRID 1736107 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([F:34])[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(=O)C(C)(C)C)=[C:13]([F:24])[CH:12]=3)=[CH:8][C:7](=[O:25])[C:6]=2[C:26]=1[NH:27]C(=O)C(C)(C)C.Cl>O1CCOCC1>[NH2:27][C:26]1[C:6]2[C:7](=[O:25])[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([F:24])[CH:12]=3)[O:10][C:5]=2[C:4]([F:34])=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 106005796,8-Difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-pivaloylamino-4H-1-benzopyran-4-one

Product 1

HCID 102671245-Amino-2-(4-amino-3-fluorophenyl)-6,8-difluoro-4H-1-benzopyran-4-oneYield 52%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.90 g of Compound 25 was dissolved in 180 ml of dioxane, 180 ml of concentrated hydrochloric acid was added and the mixture was heated at reflux for 3 hours. The reaction solution was cooled on ice, and the precipitated crystals were collected by filtration and recrystallized from methanol/chloroform to give 1.31 g (52%) of Compound 26.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe reaction solution was cooled on ice
  4. filtrationthe precipitated crystals were collected by filtration
  5. customrecrystallized from methanol/chloroform

Sources & evidence

ORD record
ord-585c3305fc5a4e0bb797c50cdcb29100
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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