Ethyl bromoacetate → HCID 13121307, compound

HRID 1702458Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:18])[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12](=[O:17])[C:9]=2[NH:10][CH:11]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CN(C)C=O.O>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][N:10]1[CH:11]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:7](=[O:18])[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12](=[O:17])[C:9]1=2)[CH3:31]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 4,9-dihydro-4,9-dioxo-1H-cyclohepta[b]pyridine-3-carboxylic acid ethyl ester (1 g, described in example 2), potassium carbonate (1 g) and ethyl bromoacetate (1 g) in dimethylformamide (DMF, 50 ml) was stirred at 25° C. for 5 hr. The reaction mixture was diluted with water and extracted with chloroform. The chloroform extract was evaporated to dryness. The residue was purified by chromatography on silica gel using chloroform-methanol (99:1) as the eluant. The appropriate fractions were pooled and crystallized from acetone to give the title compound; mp 152°-154° C.; nmr (CDCl3) δ1.3 (t, 6H), 4.3 (m, 4H), 4.85 (s, 2H), 7.0 (m, 3H), 8.2 (m, 2H); ir (CHCl3) 1740, 1730, 1690, 1630 cm-1 ; uv λ max (MeOH) 349 nm (ε12,625), 235 (18,760), 212 (25,070); Anal Calcd for C17H17NO6 : C, 61.63% H, 5.17% N, 4.23% Found: C, 61.67% H, 5.23% N, 4.25%.

Workup

extractionextracted with chloroform
extractionThe chloroform extract
customwas evaporated to dryness
customThe residue was purified by chromatography on silica gel
customcrystallized from acetone

Sources & evidence

ORD record: ord-63dd51f847ba4f5ca721364522159351
Source dataset: uspto-grants-1983_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04381304

Reaction notes

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