Hydrochloric Acid → methyl 8-iodo-2,5-dioxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carboxylate

HRID 1892169Notes

Reaction equation

[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([NH:12][C:13](=[O:20])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:3]=1.CC([O-])(C)C.[K+].O.Cl>C1COCC1>[I:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:8])[CH:15]([C:16]([O:18][CH3:19])=[O:17])[CH2:14][C:13](=[O:20])[NH:12][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 10 °C

Procedure

To a solution of methyl 4-iodo-2-[(4-methoxy-4-oxobutanoyl)amino]benzoate (24.6 g, 63 mmol) in THF (240 mL) at 10° C. was added a 1 M solution of KOt-Bu in THF (185 mL, 185 mmol) dropwise over 30 min while maintaining the temperature at 10° C. After 2.5 h, 50 mL of H2O followed by 190 mL of 1N HCl were added to bring the solution to pH=4. The resulting mixture was allowed to stir at rt for 40 min. The organic solution was separated and the aqueous solution was extracted with EtOAc (2×200 mL). The organic solutions were combined, dried over Na2SO4, filtered and concentrated to give methyl 8-iodo-2,5-dioxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carboxylate (22 g, 97%).

Workup

additionwere added
customThe organic solution was separated
extractionthe aqueous solution was extracted with EtOAc (2×200 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-c9bc5f0fa3b44fdfa7ff0e6eaea870d2
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507667B2

Reaction notes

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