Hydrochloric Acid → 2-methoxy-n-methyl-5-nitroaniline

HRID 2392666Notes

Reaction equation

HRID 2392666 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[NH:12][CH:13]=O.CSC.B.Cl>C1COCC1.CCOCC.CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[NH:12][CH3:13]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 264510N-(2-methoxy-5-nitrophenyl)formamideHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 2646152-methoxy-n-methyl-5-nitroanilineYield 95.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Methoxy-5-nitroformanilide (D84) (0.80 g, 4.1 mmole) was stirred in dry THF (30 ml) under Ar as borane dimethyl sulphide complex (2M in toluene, 5.3 ml, 10.6 mmole) was added dropwise. The mixture was stirred at reflux for 3 h, cooled and treated with methanol (5 ml). The resultant mixture was stirred for 1 h, acidified (1M HCl in ether, 5 ml), and then stirred at reflux for 1 h. It was then diluted with methanol, evaporated in vacuo, and partitioned between dil. potassium hydroxide solution and ethyl acetate. The organic portion was separated off, dried (Na2SO4) and evaporated in vacuo to give the title compound as a red-orange solid (0.71 g, 95%). 1H NMR (250 MHz, CDCl3) δ(ppm): 7.63 (dd, 1H), 7.37 (d, 1H), 6.75 (d, 1H), 4.48 (bs, 1H), 3.95 (s, 3H), 2.94 (d, 3H).

Workup

  1. additionwas added dropwise
  2. temperatureat reflux for 3 h
  3. temperaturecooled
  4. stirringstirred
  5. temperatureat reflux for 1 h
  6. customevaporated in vacuo
  7. custompartitioned between dil. potassium hydroxide solution and ethyl acetate
  8. customThe organic portion was separated off
  9. dry with materialdried (Na2SO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-ffec424ce59a427a964c9b5601004186
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

Loading…