Water → Methyl 3-amino-5-bromo-4-hydroxybenzoate

HRID 592310Notes

Reaction equation

HRID 592310 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:13]([O-])=O)[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[Sn](Cl)Cl.O>CN(C)C=O>[NH2:13][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([Br:1])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24479Stannous ChlorideHCID 14985559Methyl 3-bromo-4-hydroxy-5-nitrobenzoate

Product 1

HCID 66545110Methyl 3-amino-5-bromo-4-hydroxybenzoateYield 205%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-bromo-4-hydroxy-5-nitrobenzoate (2.00 g, 7.25 mmol) in N,N-dimethylformamide (36 mL) was slowly added tin(II) chloride dehydrate (5.50 g, 24.4 mmol). The mixture was stirred at ambient temperature. After 10 min, water was added, and organics were extracted using ethyl acetate (5×). Combined organics were dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→85% dichloromethane/methanol) gave the title compound (3.657 g, 50% purity). LC-MS [M]=246.1.

Workup

  1. extractionorganics were extracted
  2. dry with materialCombined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (100% dichloromethane→85% dichloromethane/methanol)

Sources & evidence

ORD record
ord-01012ab01e2f44cd94c2ea57d498f02c
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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