[2-(2-Chloro-benzoyl)-phenyl]-carbamic acid tert-butyl ester → 2-Amino-2'-chlorobenzophenone

HRID 2251959Notes

Reaction equation

HRID 2251959 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])(C)(C)C>Cl.CC(O)=O>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])=[O:22]

Participants

4

Reactant 1

HCID 69154584[2-(2-Chloro-benzoyl)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 761652-Amino-2'-chlorobenzophenoneYield 83%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

Dissolve [2-(2-chloro-benzoyl)-phenyl]-carbamic acid tert-butyl ester (850 mg, 2.6 mmol) in a saturated HCl in AcOH solution (10 mL, ˜3N in HCl), stir at room temperature for 3 hours. Concentrate, add CHCl3 and concentrate (3×) to remove remaining AcOH. Dissolve the residue in 20% i-PrOH/CHCl3, wash with saturated NaHCO3 solution (2×) and brine. Dry the combined organic layers over MgSO4 and concentrate to afford the title compound (495 mg, 83%): MS(IS) 232 (M+1).

Workup

  1. concentrationConcentrate
  2. additionadd CHCl3
  3. concentrationconcentrate (3×)
  4. customto remove
  5. dissolutionDissolve the residue in 20% i-PrOH/CHCl3
  6. washwash with saturated NaHCO3 solution (2×) and brine
  7. dry with materialDry the combined organic layers over MgSO4
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-109ade19ffa04f0597b3ceb3341c2d29
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

Loading…