Nitric Acid → 1-(4-Fluoro-3-nitrophenyl)ethan-1-amine

HRID 58207

Reaction equation

HRID 58207 reaction equation
[N+:1]([O-:4])(O)=[O:2].OS(O)(=O)=O.[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([NH2:19])[CH3:18])=[CH:13][CH:12]=1.[OH-].[Na+]>>[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([NH2:19])[CH3:18])=[CH:13][C:12]=1[N+:1]([O-:4])=[O:2]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 1230631-(4-Fluorophenyl)ethylamine

Product 1

HCID 552831001-(4-Fluoro-3-nitrophenyl)ethan-1-amineYield 98%

Procedure

Fuming HNO3 (0.48 ml, 10.8 mmol) was added carefully to ice bath cooled concentrated H2SO4 (3.6 ml, 68.2 mmol). To the mixture was added 1-(4-fluorophenyl)ethanamine (1.0 g, 7.2 mmol) dropwise. The reaction mixture was stirred with cooling for 50 minutes. The reaction mixture was poured into ice and basified with 3M NaOH solution (24 ml, 72.00 mmol) to about pH8.0. The alkaline solution was extracted with DCM twice. The combined organic layer was dried over Na2SO4 and evaporated to afford title compound (1.3 g, yield: 96%). 1H-NMR (400 MHz, CDCl3) δ 1.41 (d, 6H) 4.25 (q, 1H) 7.21-7.26 (m, 1H) 7.67 (ddd, 1H) 8.10 (dd, 1H)

Workup

  1. temperaturewith cooling for 50 minutes
  2. extractionThe alkaline solution was extracted with DCM twice
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-444c61759d80495580e7f0239ac9cf0b
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Linked notes

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