Acetone → 3-(3-Amino-4-nitrophenyl)-1-propanol

HRID 252816Notes

Reaction equation

HRID 252816 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:11][CH2:12][CH:13]=[O:14])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[BH4-].[Na+].CC(C)=O>O1CCCC1.CC(O)C.C(OCC)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:11][CH2:12][CH2:13][OH:14])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

7

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 597368753-(3-Amino-4-nitro-phenyl)-propionaldehyde

Product 1

HCID 597367873-(3-Amino-4-nitrophenyl)-1-propanol

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of aldehyde 80 (253 mg, 1.3 mmol) in tetrahydrofurane (1 mL) and propan-2-ol (2 mL) was treated with solid sodium borohydride (175 mg, 4.6 mmol) and stirred at −5° C. for 15 min. Acetone (5 mL) was added, stirred at the same temperature for 10 min and then diluted with ethyl acetate (100 mL), washed with 5% KHSO4 in water, then saturated NaHCO3 and finally with water, dried (MgSO4), and used for the next step without further purification.

Workup

  1. stirringstirred at the same temperature for 10 min
  2. washwashed with 5% KHSO4 in water
  3. dry with materialsaturated NaHCO3 and finally with water, dried (MgSO4)
  4. customused for the next step without further purification

Sources & evidence

ORD record
ord-17f881df57cc4512903ea2049bcbe2ff
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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