5-Bromo-2-(dimethylamino-methyleneamino)-3-methyl-benzoic acid tert-butyl ester → Tert-butyl 2-amino-5-bromo-3-methylbenzoate

HRID 583363Notes

Reaction equation

HRID 583363 reaction equation
[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=[C:9]([CH3:14])[C:8]=1[N:15]=CN(C)C)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Cl-].[Zn+2].[Cl-]>[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=[C:9]([CH3:14])[C:8]=1[NH2:15])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 540146925-Bromo-2-(dimethylamino-methyleneamino)-3-methyl-benzoic acid tert-butyl ester

Product 1

HCID 53938549Tert-butyl 2-amino-5-bromo-3-methylbenzoateYield 84.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3.52 g (10.3 mmole) of the product of Example 234 and 6.12 g (44.94 mmol) of zinc chloride in 50 ml of absolute ethanol was heated to reflux for 18 hr. The reaction mixture was concentrated in vacuo and the residue was diluted with CH2Cl2 and washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to provide 2.48 g (84%) of the desired product as a pale brown liquid. Electrospray Mass Spec 286(M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hr
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionthe residue was diluted with CH2Cl2
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e896cda5cf645d2a8667fc6016886f2
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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