3-Bromo-6-{[(tert-butoxy)carbonyl]amino}-2-methylbenzoic acid → 6-Amino-3-bromo-2-methylbenzoic acid

HRID 1725883Notes

Reaction equation

HRID 1725883 reaction equation
[Br:1][C:2]1[C:3]([CH3:19])=[C:4]([C:8]([NH:11]C(OC(C)(C)C)=O)=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]>Cl.O1CCOCC1>[NH2:11][C:8]1[C:4]([C:5]([OH:7])=[O:6])=[C:3]([CH3:19])[C:2]([Br:1])=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 688664473-Bromo-6-{[(tert-butoxy)carbonyl]amino}-2-methylbenzoic acid

Product 1

HCID 158858096-Amino-3-bromo-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of Example 104B (300 mg, 0.9 mmol) in anhydrous 4N HCl/dioxane solution (10 mL) was stirred for 2 hours and concentrated to provide the desired product as the hydrochloride salt. MS (ESI(−)) m/e 228, 230 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.34 (d, 1H), 6.66 (d, 1H), 4.44 (br s, 3H), 2.34 (s, 3H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-d5e6e5bf28b0497f9bceccbfb3eba7e6
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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