3-Bromo-o-toluidine → HCID 86687589, compound

HRID 1473531Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].CO[CH:12]=[C:13]1[C:18](=[O:19])[O:17][C:16]([CH3:21])([CH3:20])[O:15][C:14]1=[O:22]>CC(O)C>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][CH:12]=[C:13]2[C:14](=[O:22])[O:15][C:16]([CH3:20])([CH3:21])[O:17][C:18]2=[O:19])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a vial charged with 3-bromo-2-methylaniline (1.207 g, 6.49 mmol) was added IPA (12.98 ml) and 5-(methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.208 g, 6.49 mmol) respectively. The mixture was heated to 90° C. for 2 hr providing a brown solution which was cooled to room temp affording an orange precipitate which was collected by vacuum filtration affording 5-(((3-bromo-2-methylphenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.71 g, 5.03 mmol, 77% yield). This solid was transferred to a 5-20 ml microwave vial and 10 ml (0.5M 1,2-dichlorobenzene) was added and the mixture irradiated at 225° C. for 15 mins affording conversion to desired product according to LC-MS. Much precipitate was present directly following irradiation and cooling. The solid was collected via vacuum filtration and washed with heptane and dried under reduced pressure affording product as a brown solid 7-bromo-8-methylquinolin-4-ol (1.008 g, 4.23 mmol, 65.3% yield). m/z (ESI) 238.1 (M+H)+.

Workup

customproviding a brown solution which
temperaturewas cooled to room temp
customaffording an orange precipitate which
filtrationwas collected by vacuum filtration

Sources & evidence

ORD record: ord-4224b3d622704e54ad00e37a703af085
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012443B2

Reaction notes

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