HCID 58902391, compound → HCID 58902437, compound

HRID 1640138Notes

Reaction equation

HRID 1640138 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([NH:15]C(=O)C)([CH3:14])[CH3:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1>Cl.O>[NH2:15][C:12]([C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=1)[NH2:1])([CH3:14])[CH3:13]

Participants

4

Reactant 1

HCID 58902391HCID 58902391, compound

Product 1

HCID 58902437HCID 58902437, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of N-{1-[3-amino-5-(trifluoromethyl)phenyl]-1-methylethyl}acetamide (1.07 g, 4.11 mmol) in 6N HCl (20 mL) was heated at 110° C. for 18 h, then allowed to cool to rt and diluted with water. The mixture was washed with EtOAc and the aqueous solution was neutralized by the addition of 1N NaOH and washed again with EtOAc. The aqueous solution was further basified to pH 10-11 by addition of 1N NaOH and extracted with EtOAc (2×). The extracts were dried over Na2SO4, filtered and concentrated to give 3-(1-amino-1-methylethyl)-5-(trifluoromethyl)aniline as a brown oil (285 mg, 31.8%).

Workup

  1. washThe mixture was washed with EtOAc
  2. additionthe aqueous solution was neutralized by the addition of 1N NaOH
  3. washwashed again with EtOAc
  4. additionThe aqueous solution was further basified to pH 10-11 by addition of 1N NaOH
  5. extractionextracted with EtOAc (2×)
  6. dry with materialThe extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6e703ae72c2f49b1a13fb07269ffbd92
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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