Water → Methanone, (2-amino-5-chlorophenyl)(4-hydroxyphenyl)-

HRID 1701121Notes

Reaction equation

HRID 1701121 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([CH:17]=1)=[C:7]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[O:8][N:9]=2.O>C(O)(=O)C.[Fe]>[NH2:9][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:17][C:6]=1[C:7]([C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1)=[O:8]

Participants

5

Reactant 2

HCID 962WaterHCID 2463022HCID 2463022, compound

Product 1

HCID 11402375Methanone, (2-amino-5-chlorophenyl)(4-hydroxyphenyl)-

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 176Acetic AcidSolvent

Procedure

To a solution of 83.7 g (0.34 mole) of 5-chloro-3-(4-hydroxyphenyl)-2,1-benzisoxazole in 1500 ml of glacial acetic acid was added 45 g of iron filings. The mixture was stirred and heated on the steam bath for 20 min. Every 30 min. an additional 20 g of iron filings and 100 ml of water was added for 2.5 hr. After 30 min. more, the reaction mixture was filtered while hot. The collected precipitate was heated with acetic acid and filtered. The combined filtrates were diluted with ice water to precipitate 39.8 g (47%) of product, mp 170°-175°. Recrystallization from methanol-water gave yellow rods, mp 173°-178°.

Workup

  1. temperatureheated on the steam bath for 20 min
  2. filtrationthe reaction mixture was filtered while hot
  3. temperatureThe collected precipitate was heated with acetic acid
  4. filtrationfiltered
  5. additionThe combined filtrates were diluted with ice water
  6. customto precipitate 39.8 g (47%) of product, mp 170°-175°
  7. customRecrystallization from methanol-water
  8. customgave yellow rods, mp 173°-178°

Sources & evidence

ORD record
ord-390759809bec4c32b04a1e806b2126a6
Source dataset
uspto-grants-1980_03
Patent number
US04191738

Reaction notes

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