Methylamine → HCID 66942239, compound

HRID 1367661Notes

Reaction equation

[CH3:1][NH2:2].[CH2:3]([O:10][C:11]1[C:16](=[O:17])[CH:15]=[C:14]([CH3:18])O[C:12]=1[C:19]([OH:21])=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH3:1][NH2:2].[CH2:3]([O:10][C:11]1[C:16](=[O:17])[CH:15]=[C:14]([CH3:18])[N:2]([CH3:1])[C:12]=1[C:19]([OH:21])=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 70 °C

Procedure

As described previously, a 2 M methylamine solution in methanol (5.8 ml, 11.6 mmol) was added to a suspension of the 3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid (1.0 g, 3.84 mmol) in methanol (3 ml) at room temperature. The resulting solution was sealed, and then heated at 70° C. for overnight. A clear yellow solution was observed. The titled compound was obtained as a light yellow solid after solvent was removed by reducing pressure (1.02 g, 87% yield). 1H NMR (DMSO-D6) δ(ppm): 7.8 (br, 2H), 7.49 (m, 2H), 7.3 (m, 3H), 6.03 (s, 1H), 4.91 (s, 2H), 3.47 (s, 3H), 2.35 (s, 3H), 2.24 (s, 3H); MS (m/z): 274 (C15H16NO4+).

Workup

customThe resulting solution was sealed

Sources & evidence

ORD record: ord-edd41af0672c461597865c5bfb56ebf7
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893269B2

Reaction notes

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