Acetic Acid → HCID 19817699, compound

HRID 1087231Notes

Reaction equation

HRID 1087231 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[CH:4]([C:6]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10])O.C(O)(=O)C>[Pd].CO>[NH2:17][C:15]1[CH:14]=[CH:13][C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:6]([CH2:4][C:3]2[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:2]=2[F:1])[CH:16]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 19817708HCID 19817708, compound

Product 1

HCID 19817699HCID 19817699, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2'-(2,4-difluoro-α-hydroxybenzyl)-4'-nitromethanesulfonanilide (5.3 g), 10% palladium on carbon (1 g) and acetic acid (6 ml) in methanol (60 ml) was shaken under hydrogen atmosphere for 9 hours. The mixture was filtered and the filtrate was evaporated. The residue was dissolved in ethyl acetate, washed with a saturated solution of sodium bicarbonate, dried, and evaporated. The sirupy residue was recrystallized from ethanol to give crystals of 4'-amino-2'-(2,4-difluorobenzyl)methanesulfonanilide (3.2 g).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with a saturated solution of sodium bicarbonate
  5. customdried
  6. customevaporated
  7. customThe sirupy residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-5d062e52d76649a5b29cc884835ef6ae
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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