Hydrochloric Acid → 2-Methyl-2-(4-nitrophenyl)propan-1-amine

HRID 1805070Notes

Reaction equation

HRID 1805070 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)([CH3:5])[C:3]#[N:4].Cl.[OH-].[Na+]>C1COCC1>[CH3:5][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)([CH3:1])[CH2:3][NH2:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 8236152-Methyl-2-(4-nitrophenyl)propanenitrile

Product 1

HCID 186218402-Methyl-2-(4-nitrophenyl)propan-1-amineYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution of 2-methyl-2-(4-nitrophenyl)propanenitrile (670 mg, 3.5 mmol) in THF (15 mL) was added BH3 (1M in THF, 14 mL, 14 mmol) dropwise at 0° C. The mixture was warmed to room temperature and heated at 70° C. for 2 h. 1N HCl solution (2 mL) was added, followed by the addition of NaOH until pH>7. The mixture was extracted with ether and ether extract was concentrated to give 2-methyl-2-(4-nitrophenyl)propan-1-amine (610 mg, 90%), which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 8.20 (d, J=9.0 Hz, 2H), 7.54 (d, J=9.0 Hz, 2H), 2.89 (s, 2H), 1.38 (s, 6H).

Workup

  1. temperatureheated at 70° C. for 2 h
  2. extractionThe mixture was extracted with ether and ether
  3. extractionextract
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-b4d1bedf10d84669855b22be814a62ad
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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