Methylamine → 2,6-dihydroxy-N-methylbenzamide

HRID 488685Notes

Reaction equation

HRID 488685 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:3]=1[C:4]([O-])=[O:5].[CH3:12][NH2:13].C1COCC1>>[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:3]=1[C:4]([NH:13][CH3:12])=[O:5]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 178524827HCID 178524827, compound

Product 1

HCID 222719072,6-dihydroxy-N-methylbenzamide

Conditions

Temperature
100 °C

Procedure

The mixture of 2,6-dihydroxybenzoate (168 mg, 1.0 mmol) and 2 M methylamine in THF (3 mL, 6.0 mmol) in a sealed tube was heated to 100° C. overnight. The reaction mixture was then concentrated under reduced pressure and purified on silica gel eluting with hexane/ethyl acetate (1:1) to provide titled compound (67 mg). MS (ESI(+)) m/e 168 (M+H)+; 1H NMR (300 MHz, DMSO-d6) 12.57(bs, 2H), 8.82 (bs, 1H), 7.14 (t, 1H), 6.35 (d, 2H), 2.85(d, 3H).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. custompurified on silica gel eluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-3bc914aed1494607b8fe8e41be5941f7
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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