Sodium Hydroxide → ethyl 6-amino-2,2-bisfluoromethyl-2H-1-benzopyran-4-carboxylate

HRID 264822Notes

Reaction equation

HRID 264822 reaction equation
[F:1][CH2:2][C:3]1([CH2:21][F:22])[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:6]2[CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=[CH:17][C:5]=2[O:4]1.[OH-].[Na+]>C(O)C>[NH2:18][C:15]1[CH:16]=[CH:17][C:5]2[O:4][C:3]([CH2:2][F:1])([CH2:21][F:22])[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:6]=2[CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19037092ethyl 2,2-bisfluoromethyl-6-nitro-2H-1-benzopyran-4-carboxylate

Product 1

HCID 19037020ethyl 6-amino-2,2-bisfluoromethyl-2H-1-benzopyran-4-carboxylateYield 13.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 42.0 g of ethyl 2,2-bisfluoromethyl-6-nitro-2H-1-benzopyran-4-carboxylate, 88 g of stannous chloride and 500 ml of ethyl alcohol was heated while refluxing for 2 hours. A 2N aqueous solution of sodium hydroxide was added to the reaction mixture, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and then concentrated under (reduced pressure to obtain 5,2 g of ethyl 6-amino-2,2-bisfluoromethyl-2H-1-benzopyran-4-carboxylate as an oily substance.

Workup

  1. temperaturewas heated
  2. temperaturewhile refluxing for 2 hours
  3. extractionby extracting with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under (reduced pressure

Sources & evidence

ORD record
ord-4904dceed09b407faaf0133f4df99657
Source dataset
uspto-grants-1997_07
Patent number
US05646310

Reaction notes

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