Methanol → HCID 19875881, compound

HRID 1886349Notes

Reaction equation

HRID 1886349 reaction equation
[CH3:1][CH:2]([CH3:16])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH3:12])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)=[O:4].CO.[BH4-].[Na+]>O>[CH3:12][NH:11][C:8]1[CH:9]=[CH:10][C:5]([CH:3]([CH:2]([CH3:16])[CH3:1])[OH:4])=[CH:6][C:7]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 19875829HCID 19875829, compound

Product 1

HCID 19875881HCID 19875881, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 30 parts of intermediate 45, namely 2-methyl-1-[4-(methylamino)-3-nitrophenyl]-1-propanone in 320 parts of methanol were added dropwise 15 parts of sodium tetrahydroborate (the temperature was kept at 20° C.). Upon complete addition, stirring was continued for 30 minutes at room temperature. The reaction mixture was poured into water and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated to dry, yielding 30 parts (100%) of 4-(methylamino)-α-(1-methylethyl)-3-nitrobenzenemethanol as an oily residue (interm. 46).

Workup

  1. customwas kept at 20° C.
  2. additionUpon complete addition
  3. extractionthe product was extracted with trichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customto dry

Sources & evidence

ORD record
ord-d1814580444849b5b0673b1f29bad03a
Source dataset
uspto-grants-1992_09
Patent number
US05151421

Reaction notes

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