Water → HCID 22226936, compound

HRID 1745916Notes

Reaction equation

HRID 1745916 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C([O-])([O-])=O.[Cs+].[Cs+].[Br-].[CH:19]1([CH3:22])[CH2:21][CH2:20]1.O>CN(C=O)C>[CH:19]1([CH2:22][O:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=2)[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 37588824-Amino-3-NitrophenolHCID 22042231HCID 22042231, compound

Product 1

HCID 22226936HCID 22226936, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Amino-3-nitrophenol (26.00 g, 165.5 mMol) was dissolved in 200 mL of anhydrous DMF under an atmosphere of dry N2. The reaction mixture was then cooled to 0° C. and to this mixture was added Cs2CO3 (64.7 g, 199 mMol), and cyclopropyl methane bromide (17.7 mL, 182 mMol). After stirring for 15 minutes, the reaction mixture was then warmed up to ambient temperature and then stirred overnight. The reaction mixture is then poured into 800 mL of water. The precipitate was collected via suction filtration and partitioned between DCM and aqueous 0.1 N NaOH. The DCM layer was saved and washed again aqueous 0.1 N NaOH, then with brine, dried over Na2SO4, filtered and concentrated under vacuum to give 31.52 g of 4-cyclopropylmethoxy-2-nitro-phenylamine 133A as an orange solid.

Workup

  1. temperaturethe reaction mixture was then warmed up to ambient temperature
  2. stirringstirred overnight
  3. filtrationThe precipitate was collected via suction filtration
  4. custompartitioned between DCM and aqueous 0.1 N NaOH
  5. washwashed again aqueous 0.1 N NaOH
  6. dry with materialwith brine, dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7e556eca6ba94eefad40a7574fab7b9c
Source dataset
uspto-grants-2006_03
Patent number
US07019147B1

Reaction notes

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