(2-Amino-4-chlorophenyl)methanol → N-(5-chloro-2-hydoxymethylphenyl)formamide

HRID 350603Notes

Reaction equation

HRID 350603 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].[CH:11](OCC#N)=[O:12]>O1CCCC1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:9][OH:10])=[C:2]([NH:1][CH:11]=[O:12])[CH:7]=1

Participants

4

Reactant 2

HCID 4134900(2-Amino-4-chlorophenyl)methanolHCID 4205685(Formyloxy)acetonitrile

Product 1

HCID 12083233N-(5-chloro-2-hydoxymethylphenyl)formamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.00 g of (2-amino-4-chlorophenyl)methanol, 2.73 g of cyanomethyl formate and 0.04 g of 4-N,N-dimethylaminopyridine in 50 ml of anhydrous tetrahydrofuran was stirred for 72 hours at 20° C. The solvent was then evaporated in vacuo and the residue was taken up in 50 ml of ethyl acetate. The solution was washed in succession twice with in each case 100 ml of 0.01 N hydrochloric acid and saturated sodium chloride solution, dried over sodium sulfate and then concentrated by evaporation in vacuo. The residue was purified by flash chromatography on silica gel with ethyl acetate/cyclohexane (2/1) as eluent. 1.41 g (24% of theory) of the title compound was thereby obtained in the form of slightly yellowish crystals.

Workup

  1. customThe solvent was then evaporated in vacuo
  2. washThe solution was washed in succession twice with in each case 100 ml of 0.01 N hydrochloric acid and saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated by evaporation in vacuo
  5. customThe residue was purified by flash chromatography on silica gel with ethyl acetate/cyclohexane (2/1) as eluent

Sources & evidence

ORD record
ord-80d56597d06c4e7d895c9a203c1b9c88
Source dataset
uspto-grants-2007_02
Patent number
US07183274B2

Reaction notes

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