Sodium Bicarbonate → 8-Hydroxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b]fluoren-5-one

HRID 2275282Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[O:19])[C:17]3[C:16]4[N:15]=[CH:14][CH:13]=[CH:12][C:11]=4[O:10][C:9]=3[C:8]([CH3:21])([CH3:20])[C:7]=2[CH:22]=1.Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[O:19])[C:17]3[C:16]4[N:15]=[CH:14][CH:13]=[CH:12][C:11]=4[O:10][C:9]=3[C:8]([CH3:20])([CH3:21])[C:7]=2[CH:22]=1

Participants

Conditions

Temperature: 178 °C

Procedure

Mixture of 8-methoxy-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b]fluoren-5-one (Compound GT15-4, 25 mg) and pyridine hydrochloric acid salt (492 mg) was stirred and heated at 178° C. overnight. The reaction mixture was cooled, and added with water. The mixture was neutralized with saturated aqueous solution of sodium bicarbonate and extracted with DCM. The organic layer was washed with saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (DCM/MeOH) to obtain the title compound (13 mg, 54%).

Workup

temperatureThe reaction mixture was cooled
extractionextracted with DCM
washThe organic layer was washed with saturated brine
concentrationconcentrated under reduced pressure
customThe resulting residues were purified by silica gel column (DCM/MeOH)

Sources & evidence

ORD record: ord-8590ae20e2d7476e80c47dbd6fbf7e2f
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126931B2

Reaction notes

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