Toluene → 2-(2-fluorobiphenyl-4-yl)-N-methylpropanohydroxamic acid

HRID 649239Notes

Reaction equation

HRID 649239 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:12])[C:9](Cl)=[O:10])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Cl)(=O)C(Cl)=O.C1(C)C=CC=CC=1.Cl.[CH3:33][NH:34][OH:35]>O1CCCC1.O.C(N(CC)CC)C>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:12])[C:9]([N:34]([CH3:33])[OH:35])=[O:10])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 65578Oxalyl chlorideHCID 77906N-methylhydroxylamine hydrochlorideHCID 11032707Flurbiprofen Acid Chloride

Product 1

HCID 156705292-(2-fluorobiphenyl-4-yl)-N-methylpropanohydroxamic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

2-(2-Fluorobiphenyl-4-yl)propionic acid chloride (prepared in the normal manner from 1.75 g of acid, ca 1 ml of oxalyl chloride, toluene, and 3 drops of N,N-(dimethylformamide) was dissolved in tetrahydrofuran (30 ml) and added over 5-10 minutes to a solution of N-Methylhydroxylamine hydrochloride (ca 2 g) in water (5 ml) containing triethylamine (5 ml) at 0°. Solvent was evaporated, and neutral material was isolated with ethyl acetate. Recrystallization from ether-light petroleum (b.pt. 40°-60°) afforded 2-(2-fluorobiphenyl-4-yl)-N-methylpropanohydroxamic acid (1.25 g), m.pt. 125°-126° C.

Workup

  1. customSolvent was evaporated
  2. customneutral material was isolated with ethyl acetate
  3. customRecrystallization from ether-light petroleum (b.pt. 40°-60°)

Sources & evidence

ORD record
ord-20759e6e1e2c4715a243d6d81a477b3d
Source dataset
uspto-grants-1988_04
Patent number
US04738986

Reaction notes

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