Phosphoric Acid → 2-[(2,6-Dichloro-3-methylphenyl)amino]phenylmethanol

HRID 343884Notes

Reaction equation

HRID 343884 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]([NH:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[C:16](O)=[O:17])[C:7]=1[Cl:8].[H-].[H-].[H-].[H-].[Li+].[Al+3].OP(O)(O)=O>C1COCC1>[Cl:8][C:7]1[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]([Cl:19])[C:6]=1[NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=1[CH2:16][OH:17]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 4037Meclofenamic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 150273752-[(2,6-Dichloro-3-methylphenyl)amino]phenylmethanolYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of meclofenamic acid (4.27 g, 13.4 mmol) in THF (75 mL) at 0° C. was added LiAlH4 (1.02 g, 26.8 mmol) in portions over 0.5 hour. The mixture was maintained cold for 2 hrs after which it was slowly added to a cold solution of H3PO4 (1M, 100 mL) and extracted with ethyl ether (3×75 mL). The combined organic layers were washed with water and brine, dried over MgSO4. filtered, and evaporated in vacuo. Purification by chromatography on silica gel (9:1 hexanes/ethyl acetate) afforded 2.1 g (56%) of 2-[(2,6-dichloro-3-methylphenyl)amino]phenylmethanol as an off white solid.

Workup

  1. temperatureThe mixture was maintained cold for 2 hrs after which it
  2. extractionextracted with ethyl ether (3×75 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by chromatography on silica gel (9:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-9a22b0c6c5dd4df999a827f7e6de4f5c
Source dataset
uspto-grants-1999_01
Patent number
US05863946

Reaction notes

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