Acetic Acid → 298185-50-9

HRID 365531Notes

Reaction equation

HRID 365531 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[CH3:11])[NH2:7].C(O)(=O)C.[CH3:16][C:17]([CH3:19])=O.C([O-])(=O)C.[Na+]>CCCCCC.CCOCC.O.C(O)C>[Br:3][C:4]1[CH:5]=[C:6]([NH:7][CH:17]([CH3:19])[CH3:16])[CH:8]=[CH:9][C:10]=1[CH3:11]

Participants

10

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 82187Benzenamine, 3-bromo-4-methyl-HCID 517045Sodium AcetateHCID 4311764Sodium borohydride

Product 1

HCID 23291925298185-50-9

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (30.5 g, 806.2 mmol) was added slowly over 3 hours to a stirring mixture of 3-bromo-4-methylaniline (30 g, 161.2 mmol), ethanol (110 mL), acetic acid (92 mL, 1.6 mol), water (265 mL), acetone (66 mL, 892.2 mmol), and sodium acetate (29.2 g, 214.9 mmol). The solution was stirred at 0° C. for 1 hour. The reaction mixture was poured into the 1:1 mixture of ether and hexane containing 2N KOH. The layers were separated and aqueous layer was extracted with ether/hexane (1:1). The combined organic layers were washed once with water and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was used directly for the next reaction without further purification:

Workup

  1. customThe layers were separated
  2. extractionaqueous layer was extracted with ether/hexane (1:1)
  3. washThe combined organic layers were washed once with water and brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was used directly for the next reaction without further purification

Sources & evidence

ORD record
ord-ca10360f72ac4900969b9c0ba2d5c261
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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