Ethyl 4-bromobutyrate → HCID 13558283, compound

HRID 637564Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7]Br)[CH3:2].[NH2:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=1[C:21](=[O:23])[CH3:22].C([O-])(O)=O.[Na+]>C(N(CC)CC)C.C(Cl)(Cl)Cl>[C:4]([CH2:5][CH2:6][CH2:7][NH:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=1[C:21](=[O:23])[CH3:22])([O:3][CH2:1][CH3:2])=[O:9]

Participants

Conditions

Temperature: 110 °C

Procedure

Ethyl-4-bromobutyrate (190.7 g, 978 mM) was added with stirring to 2'-amino-4',5'-dimethoxyacetophenone (31.8 g, 163 mM) in triethylamine (33.9 mM) and the reaction mixture was heated at 110° C. for one hour. After cooling to room temperature 100 mL of 2% NaHCO3 was added and the reaction mixture was stirred for sixteen hours. A yellow solid formed which was dissolved in CHCl3 (250 mL). The aqueous phase was extracted with CHCl3 (4×200 mL), the organic extracts were combined and dried over MgSO4, filtered, and the solvent removed in vacuo to give a semisolid residue. The residue was chromatographed on SilicAR CC-7 and the appropriate fractions were crystallized upon standing from ether to afford the title compound in 62% yield, ,mp 74°-76° C.

Workup

additionwas added
customA yellow solid formed which
extractionThe aqueous phase was extracted with CHCl3 (4×200 mL)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent removed in vacuo
customto give a semisolid residue
customThe residue was chromatographed on SilicAR CC-7
customthe appropriate fractions were crystallized

Sources & evidence

ORD record: ord-4d9ec60bef154c18ad310cd90d0728f2
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04556739

Reaction notes

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