Ethanol → HCID 29054512, compound

HRID 1776467Notes

Reaction equation

HRID 1776467 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1.CCO.[CH3:17][NH2:18]>>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH:18][CH3:17])=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 115796484-(Bromomethyl)-1-methoxy-2-nitrobenzene

Product 1

HCID 29054512HCID 29054512, compoundYield 100%

Procedure

4-(bromomethyl)-1-methoxy-2-nitrobenzene (276 mg, 1.122 mmol) was dissolved in methanamine in EtOH (33% w/w, 8 ml, 64.5 mmol) and stirred at RT for 1.5 hours. The mixture was evaporated to dryness and diluted with WATER/brine. The aqueous phase was extracted twice with EtOAc. NaHCO3 sat. sol. was added until basic pH, and the aqueous phase was extracted twice with DCM. The combined organic layers were dried and evaporated under vacuum to give 1-(4-methoxy-3-nitrophenyl)-N-methylmethanamine (220 mg, 1.121 mmol, 100% yield, MS/ESI+ 197.1 [MH]+) that was used in the next step without further purification.

Workup

  1. customThe mixture was evaporated to dryness
  2. additiondiluted with WATER/brine
  3. extractionThe aqueous phase was extracted twice with EtOAc
  4. additionNaHCO3 sat. sol. was added until basic pH
  5. extractionthe aqueous phase was extracted twice with DCM
  6. customThe combined organic layers were dried
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-d251d96a6220442098d2174d5bc7547a
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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