Methylamine → 2,6-Dihydroxybenzamide

HRID 1375663

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].C[NH2:13].C1COCC1>>[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:3]=1[C:4]([NH2:13])=[O:5]

Participants

Reactant 3

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 178524827HCID 178524827, compound

Product 1

HCID 766022,6-Dihydroxybenzamide

Conditions

Temperature: 100 °C

Procedure

The mixture of 2,6-dihydroxybenzoate (168 mg, 1.0 mmol) and 2M methylamine in THF (3 mL, 6.0 mmol) in a sealed tube was heated at 100° C. overnight. The reaction mixture was then concentrated under reduced pressure and purified by flash chromatography on silica gel with hexane/ethyl acetate (1:1) to provide the titled compound (67 mg) as white solid. MS (ESI(+)) m/e 168 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 12.57(bs, 2H), 8.82 (bs, 1H), 7.14 (t, J=8.1 Hz 1H), 6.35 (d, J=8.5 Hz, 2H), 2.85(d, J=4.7 Hz, 3H).

Workup

concentrationThe reaction mixture was then concentrated under reduced pressure
custompurified by flash chromatography on silica gel with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record: ord-da5fe825a751428e93e4036d6b0144b8
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169797B2

Linked notes

Loading…