Acetone → HCID 57436583, compound

HRID 730931Notes

Reaction equation

HRID 730931 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=2[O:18][CH3:19])[CH:6]=[CH:7][CH:8]=1.[BH4-].[Na+].[CH3:22][C:23]([CH3:25])=O>C(Cl)Cl>[CH:23]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=2[O:18][CH3:19])[CH:6]=[CH:7][CH:8]=1)([CH3:25])[CH3:22]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 57436580HCID 57436580, compound

Product 1

HCID 57436583HCID 57436583, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Aminomethylphenyl)-4-nitroanisole (0.10 g, 0.39 mmol) was dissolved in anhydrous acetone (25 mL). The solution was distilled at atmospheric pressure until the volume was reduced to approximately 5 mL. The solution was then distilled under reduced pressure at room temperature to remove the last traces of acetone. The resultant oil was re-dissolved in CH2Cl2/MeOH (2 mL: 1 mL). Sodium borohydride (44 mg, 3 equiv) was added, and the reaction mixture stirred at room temperature for 2 h. The solution was then diluted with CH2Cl2 (10 mL), extracted with 1M NaOH (4×5 mL), dried (Na2SO4), and evaporated to afford 2-(3-(N-isopropylamino)methylphenyl)-4-nitroanisole (120 mg, 0.39 mmol, 100%).

Workup

  1. distillationThe solution was distilled at atmospheric pressure until the volume
  2. distillationThe solution was then distilled under reduced pressure at room temperature
  3. customto remove the last traces of acetone
  4. dissolutionThe resultant oil was re-dissolved in CH2Cl2/MeOH (2 mL: 1 mL)
  5. extractionextracted with 1M NaOH (4×5 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-ae5a7c8b53644760aaa465e17d32c012
Source dataset
uspto-grants-2009_09
Patent number
US07582765B2

Reaction notes

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