Benzoic acid, 4-amino-3-hydroxy-, methyl ester → HCID 66690714, compound

HRID 592314Notes

Reaction equation

HRID 592314 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].[Br:13]NC(=O)CCC(N)=O>ClCCl.CN(C)C=O>[NH2:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:11]=1[Br:13]

Participants

5

Reactant 2

HCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl esterHCID 9834204N-Bromosuccinamide

Product 1

HCID 66690714HCID 66690714, compoundYield 32.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-amino-3-hydroxybenzoate (2.5 g, 15.0 mmol) in dichloromethane (71 mL) and N,N-dimethylformamide (3.6 mL) was added N-bromosuccinamide (2.93 g, 16.5 mmol). The mixture was stirred at ambient temperature. After 15 min, the mixture was quenched with sat. sodium sulfite. Hydrochloric acid (1.0 M) was added and the mixture was extracted with dichloromethane (3×). The combined organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→100% ethyl acetate) gave the title compound (1.2 g). LC-MS [M]=246.0.

Workup

  1. customthe mixture was quenched with sat. sodium sulfite
  2. additionHydrochloric acid (1.0 M) was added
  3. extractionthe mixture was extracted with dichloromethane (3×)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (100% hexanes→100% ethyl acetate)

Sources & evidence

ORD record
ord-34f168478f4743248e163cdbbe5c483e
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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