Hydrochloric Acid → 5-Amino-6,8-difluoro-2-[3-fluoro-4-[(3-phthalimidopropyl)amino]phenyl]-4H-1-benzopyran-4-one

HRID 1736110Notes

Reaction equation

HRID 1736110 reaction equation
C([N:4]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:26][C:27]3[C:35]([F:36])=[CH:34][C:33]([F:37])=[C:32]([NH2:38])[C:28]=3[C:29](=[O:31])[CH:30]=2)=[CH:21][C:20]=1[F:39])[CH2:5][CH2:6][CH2:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18])(=O)C.Cl.[OH-].[Na+]>O1CCOCC1>[NH2:38][C:32]1[C:28]2[C:29](=[O:31])[CH:30]=[C:25]([C:22]3[CH:23]=[CH:24][C:19]([NH:4][CH2:5][CH2:6][CH2:7][N:8]4[C:12](=[O:13])[C:11]5=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]5[C:9]4=[O:18])=[C:20]([F:39])[CH:21]=3)[O:26][C:27]=2[C:35]([F:36])=[CH:34][C:33]=1[F:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 153469942-[4-[N-Acetyl-N-(3-phthalimidopropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one

Product 1

HCID 153469955-Amino-6,8-difluoro-2-[3-fluoro-4-[(3-phthalimidopropyl)amino]phenyl]-4H-1-benzopyran-4-oneYield 87.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.0 g of Compound 28 was dissolved in 12 ml of dioxane, 8 ml of concentrated hydrochloric acid was added and the mixture was heated at reflux for 4.3 hours. The reaction solution was cooled on ice and adjusted to pH 8 by addition of a 10N aqueous solution of sodium hydroxide thereto, and the precipitated crystals were collected by filtration to give 805 mg (87%) of Compound 29.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4.3 hours
  3. temperatureThe reaction solution was cooled on ice
  4. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-a5378e14bd2a453b835174dfd3c1d8df
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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