Ammonia → HCID 21831361, compound

HRID 1601399Notes

Reaction equation

HRID 1601399 reaction equation
[O:1]1[CH:7]2[CH:2]1[C:3]([CH2:17][F:18])([CH2:15][F:16])[O:4][C:5]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:6]=12.[NH3:19]>C(O)C>[NH2:19][CH:7]1[C:6]2[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:5]=2[O:4][C:3]([CH2:17][F:18])([CH2:15][F:16])[CH:2]1[OH:1]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21831317HCID 21831317, compound

Product 1

HCID 21831361HCID 21831361, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.53 g of 3,4-epoxy-2,2-bisfluoromethyl-3,4-dihydro-6-nitro-2H-1-benzopyran, 15 ml of a concentrated aqueous ammonia solution and 15 ml of ethanol was stirred at room temperature for 42 hours. The solvent was distilled off and methylene chloride was added thereto. The mixture was extracted with 1N hydrochloric acid and 2N sodium hydroxide was added to an aqueous layer to form an alkaline solution. The solution was extracted with methylene chloride and the organic layer was washed with water and dried. The solvent was distilled off and the resultant residue was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain 0.32 g of 4-amino-2,2-bisfluoromethyl-3,4-dihydro-6-nitro-2H-1-benzopyran-3-ol represented by the following formula having a melting point of 174-177° C. (decomp.).

Workup

  1. distillationThe solvent was distilled off
  2. additionmethylene chloride was added
  3. extractionThe mixture was extracted with 1N hydrochloric acid and 2N sodium hydroxide
  4. additionwas added to an aqueous layer
  5. customto form an alkaline solution
  6. extractionThe solution was extracted with methylene chloride
  7. washthe organic layer was washed with water
  8. customdried
  9. distillationThe solvent was distilled off
  10. customthe resultant residue was recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-c0815ccc934f40019314b0fa2c6cfaa1
Source dataset
uspto-grants-1999_11
Patent number
US05977167

Reaction notes

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