Hydrogen Bromide → N-(4-Oxo-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

HRID 1155642Notes

Reaction equation

[CH:1]1([NH:11][C:12](=[O:14])[CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Br.[O:16]=O>C(O)(=O)C.C(C(C)=O)C(C)C>[O:16]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]([NH:11][C:12](=[O:14])[CH3:13])[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 62 °C

Procedure

A mixture of N-(1,2,3,4-tetrahydro-1-naphthyl)-acetamide (30 g), cobaltous acetate tetrahydrate (13.12 g), 30% hydrobromic acid in acetic acid (4.28 g), methyl isobutyl ketone (400 ml) and acetic acid (100 ml) is stirred and oxygen is introduced via a capillary gas dispersion tube. The mixture is heated gradually to 62° C. and the reaction is run 17 hours at 62° C. The reaction mixture is then cooled, the oxygen flow terminated and water (500 ml) is added. The mixture is extracted with chloroform (500 ml and 2×300 ml), the chloroform extracts are combined, washed with saturated sodium chloride solution and evaporated to dryness in vacuo. Benzene (200 ml) is added to the residue, the solution is filtered and the filtrate evaporated to dryness in vacuo to afford 40.3 g (damp) of the title compound.

Workup

temperatureThe reaction mixture is then cooled
customthe oxygen flow terminated
additionwater (500 ml) is added
extractionThe mixture is extracted with chloroform (500 ml and 2×300 ml)
washwashed with saturated sodium chloride solution
customevaporated to dryness in vacuo
additionBenzene (200 ml) is added to the residue
filtrationthe solution is filtered
customthe filtrate evaporated to dryness in vacuo

Sources & evidence

ORD record: ord-7d175949354749c0bb949b2d0914230f
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04332724

Reaction notes

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