Ethyl Acetate → HCID 178518334, compound

HRID 1672463Notes

Reaction equation

[NH2:1][C:2]1[C:11]([O:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[O:19]([C:21]#[N:22])[K].C(OCC)(=O)C>CC(O)=O.O>[O:16]1[CH2:17][CH2:18][CH:13]([O:12][C:11]2[CH:10]=[CH:9][CH:8]=[C:3]3[C:2]=2[N:1]=[C:21]([OH:19])[N:22]=[C:4]3[OH:6])[CH2:14][CH2:15]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 2-amino-3-(tetrahydro-2H-pyran-4-yloxy)benzoate (18 g, 0.071 mol) in AcOH (180 mL) was added a solution of KOCN (11.47 g, 142 mmol) in water (22 mL) at 60° C. Then the mixture was heated at 80° C. for 40 h. TLC (petroleum ether:ethyl acetate=1:1) showed the reaction was complete. Then the mixture was concentrated in vacuo. The residue was diluted with water (200 mL). The precipitate was filtered to give the title compound (9 g, 42%) as a white solid. 1H NMR (400 MHz, DMSO): δ 11.354 (s, 1H), 10.491 (s, 1H), 7.539 (d, 1H), 7.455 (d, 1H), 7.191 (t, 1H), 4.732 (m, 1H), 4.006 (m, 2H), 3.535 (m, 3H), 2.023 (m, 2H), 1.842 (m, 2H)

Workup

concentrationThen the mixture was concentrated in vacuo
additionThe residue was diluted with water (200 mL)
filtrationThe precipitate was filtered

Sources & evidence

ORD record: ord-6918da2aea02475ab6d3ad8865f4f617
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998978B2

Reaction notes

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