Acetic Acid → 2,6-dimethyl-4-[N-methyl-N-(1-phenyl-1H-pyrazol-3-yl) amino]phenol

HRID 22275Notes

Reaction equation

HRID 22275 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:13]=[CH:12][N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:10]=2)[CH:5]=[C:4]([CH3:20])[C:3]=1[OH:21].[C:22](O)(=O)C.C=O.C([BH3-])#N.[Na+]>C(#N)C>[CH3:1][C:2]1[CH:7]=[C:6]([N:8]([CH3:22])[C:9]2[CH:13]=[CH:12][N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:10]=2)[CH:5]=[C:4]([CH3:20])[C:3]=1[OH:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 199279132,6-dimethyl-4-(1-phenyl-1H-pyrazol-3-yl) aminophenol

Product 1

HCID 540328202,6-dimethyl-4-[N-methyl-N-(1-phenyl-1H-pyrazol-3-yl) amino]phenol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2,6-dimethyl-4-(1-phenyl-1H-pyrazol-3-yl)amino phenol (8 g), acetic acid (2.8 ml), and aqueous 40% formaldehyde (3.1 ml) in acetonitrile (40 ml) was added sodium cyanoborohydride (5.4 g). After 2 hours the mixure was quenched with water and extracted with dichloromethane. The organic phase was washed with aqueous sodium bicarbonate solution, then water, dried, evaporated and chromatographed (silica, dichloromethane) to give the title product (3 g), mp 139°-140° (from ethanol).

Workup

  1. customAfter 2 hours the mixure was quenched with water
  2. extractionextracted with dichloromethane
  3. washThe organic phase was washed with aqueous sodium bicarbonate solution
  4. dry with materialwater, dried
  5. customevaporated
  6. customchromatographed (silica, dichloromethane)

Sources & evidence

ORD record
ord-84a8aa784eb9465c874d65b7ee256831
Source dataset
uspto-grants-1995_06
Patent number
US05428044

Reaction notes

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