Hydrochloric Acid → HCID 67247636, compound

HRID 2273180Notes

Reaction equation

C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][C:18]1[O:17][CH2:16][C:15](C(O)=O)=[CH:14][C:13]2=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.Cl>ClCCl.C1(C)C=CC=CC=1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][C:18]1[O:17][CH2:16][C:15](=[O:34])[CH2:14][C:13]2=1

Participants

Conditions

Temperature: 90 °C

Procedure

Triethylamine (13 μL, 0.09 mmol, 1.2 eq) is added at room temperature to a stirred solution of 6-methoxy-2H-1-oxa-9-aza-phenanthrene-3-carboxylic acid (20 mg, 0.08 mmol, 1.0 eq) in dichloromethane (1 mL), followed by a solution of diphenylphosphoryl azide (23 mg, 0.08 mmol, 1.0 eq) in toluene (1.5 mL). After 1 h 30 stirring at 80° C., 6M hydrochloric acid aqueous solution (0.5 mL) is added and the resulting mixture is heated at 90° C. for 2 hours. The reaction mixture is then cooled down to room temperature and extracted with ethyl acetate (3×10 mL) and saturated sodium hydrogen carbonate aqueous solution (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: ethyl acetate) to afford 6-methoxy-4H-1-oxa-9-aza-phenanthrene-3-one as a yellow semisolid (5 mg, 28% yield).

Workup

temperatureThe reaction mixture is then cooled down to room temperature
extractionextracted with ethyl acetate (3×10 mL) and saturated sodium hydrogen carbonate aqueous solution (10 mL)
dry with materialThe combined organic layers are dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto give a residue that
customis purified by column chromatography (silica gel, eluent: ethyl acetate)

Sources & evidence

ORD record: ord-9bc9164af13741c79f54a7ef25d051f7
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120822B2

Reaction notes

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