Cyclopropylamine → HCID 117843142, compound

HRID 2209035Notes

Reaction equation

HRID 2209035 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[CH:13]1([NH2:16])[CH2:15][CH2:14]1>O1CCOCC1.CCOC(C)=O.O.[Cl-].[Na+].O>[CH:13]1([NH:16][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=2[O:11][CH3:12])[CH2:15][CH2:14]1

Participants

7

Reactant 2

HCID 69828CyclopropylamineHCID 177502992-Bromo-3-nitroanisole

Product 1

HCID 117843142HCID 117843142, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-bromo-1-methoxy-3-nitrobenzene (10.6 g, 45.7 mmol) and cyclopropylamine (16 mL, 230 mmol) were dissolved in 1,4-dioxane (50 mL). The stirred mixture was heated mixture in sealed flask to 115 C. After 66 h, mixture was cooled to r.t. and was diluted with EtOAc (100 mL), water (100 mL) and brine (50 mL). The phases were separated and extracted with EtOAc (100 mL). The combined organic phase was dried over Na2SO4, filtered, and concentrated. The concentrate was purified by silica gel chromatography (0-20% EtOAc in hexanes) to afford N-cyclopropyl-2-methoxy-6-nitroaniline. LCMS-ESI+ (m/z): [M+H]+ calcd for C10H13N2O3: 209.09; found: 209.96.

Workup

  1. temperatureThe stirred mixture was heated mixture in sealed flask to 115 C
  2. customThe phases were separated
  3. extractionextracted with EtOAc (100 mL)
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-eb838c200d384959acd66080375ec74f
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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