Hydrochloric Acid → (2-Amino-5-fluorophenyl)-(2-chlorophenyl)methanol

HRID 747604Notes

Reaction equation

HRID 747604 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])=[O:12])([O-])=O.[Sn].Cl>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[OH:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 68569266(2-Nitro-5-fluorophenyl)(2-chlorophenyl)methanone

Product 1

HCID 68567746(2-Amino-5-fluorophenyl)-(2-chlorophenyl)methanolYield 100.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 0.5 g of (2-nitro-5-fluorophenyl)(2-chlorophenyl)methanone dissolved in 10 ml of ethanol are added 0.44 g of tin and 1.5 ml of 12M hydrochloric acid, and the mixture is left for 3 hours at room temperature. The reaction medium is concentrated and the residue is taken up in ethyl acetate and washed with 2M sodium hydroxide solution and then with saturated ammonium chloride solution. The organic phase is dried over anhydrous sodium sulfate and concentrated to give 0.453 g of the expected product.

Workup

  1. concentrationThe reaction medium is concentrated
  2. washwashed with 2M sodium hydroxide solution
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a38e9f99595b444aaffe62b79dc614b5
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

Loading…