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

HRID 1067648Notes

Reaction equation

HRID 1067648 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH2:21][F:22])([CH2:19][F:20])[CH:7]=1)=[O:5])[CH3:2].[Cl-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:11]2[CH:12]=[C:13]([NH2:16])[CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH2:21][F:22])([CH2:19][F:20])[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 5234Sodium ChlorideHCID 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 2,2-bisfluoromethyl-6-nitro-2H-1-benzopyran-4-carboxylic acid ethyl ester, 88 g of stannous chloride and 500 ml of ethyl alcohol was heated to reflux for 2 hours. The reaction mixture was combined with an aqueous 2N sodium chloride solution and extracted with ethyl acetate. The organic layer was washed with saturated saline, then dried over sodium sulfate and concentrated under reduced pressure to give 5.2 g of 6-amino-2,2-bisfluoromethyl-2H-1-benzopyran-4-carboxylic acid ethyl ester as an oil;

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-76511a1ac55044028b7f56406f5e73b6
Source dataset
uspto-grants-2001_06
Patent number
US06248777B1

Reaction notes

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