Isopropyl iodide → HCID 68412169, compound

HRID 220243Notes

Reaction equation

HRID 220243 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].C([O-])([O-])=O.[K+].[K+].I[CH:19]([CH3:21])[CH3:20]>CN(C=O)C>[CH:19]([O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH2:1])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 68412169HCID 68412169, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5 g of 2-amino-3-nitrophenol in 10 mL DMF were added 4.9 g of K2CO3 and 3.6 mL of 2-iodopropane. The reaction mixture was stirred at rt overnight and then concentrated in vacuo. The residue was taken up in sat. aq. NH4Cl and extracted with EtOAc (3 times). The organic phases were combined, washed with water, brine, dried over MgSO4 and concentrated in vacuo. Purification by CC with EtOAc-Hept (2:8) afforded 5.2 g of 2-isopropoxy-6-nitro-phenylamine as orange oil.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with EtOAc (3 times)
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by CC with EtOAc-Hept (2:8)

Sources & evidence

ORD record
ord-7f17c702daed424fab6fd6d1551b886b
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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