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

HRID 1736122Notes

Reaction equation

HRID 1736122 reaction equation
C([N:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[C:25]([F:26])=[CH:24][C:23]([F:27])=[C:22]([NH2:28])[C:18]=3[C:19](=[O:21])[CH:20]=2)=[CH:11][C:10]=1[F:29])[CH2:5][CH2:6][CH2:7][Cl:8])(=O)C.Cl.O>O1CCOCC1>[NH2:28][C:22]1[C:18]2[C:19](=[O:21])[CH:20]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([NH:4][CH2:5][CH2:6][CH2:7][Cl:8])=[C:10]([F:29])[CH:11]=3)[O:16][C:17]=2[C:25]([F:26])=[CH:24][C:23]=1[F:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19434902HCID 19434902, compound

Product 1

HCID 194348465-amino-2-[4-(3-chloropropylamino)-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-oneYield 49%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

508 mg (1.20 mmol) of the resulting 2-[4-[N-acetyl-N-(3-chloropropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one was dissolved in 30 ml of dioxane, 30 ml of concentrated hydrochloric acid was added and the mixture was stirred for 3 hours under heating at reflux. The reaction solution was cooled on ice and adjusted to pH 8 by addition of water thereto, and the precipitated crystals were collected by filtration. The crystals were purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give 224 mg (49%) of 5-amino-2-[4-(3-chloropropylamino)-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one.

Workup

  1. temperatureunder heating
  2. temperatureat reflux
  3. temperatureThe reaction solution was cooled on ice
  4. filtrationthe precipitated crystals were collected by filtration
  5. customThe crystals were purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-99abc3c764c647b1a8ef37c5409fb541
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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