Water → 1-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

HRID 1406172Notes

Reaction equation

[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](O)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].P(Br)(Br)([Br:22])=O.O>C(#N)C>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:22])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

2 g (7.7 mmol) of 1,4-Dihydroxy-isoquinoline-3-carboxylic acid butyl ester (from Example D-20b) dissolved in 100 ml of acetonitrile. 15.4 g (53.6 mmol) of phosphorous oxybromide added to solution and mixture stirred at 80° C. for 64 h. 100 ml of water was added to mixture, and mixture was removed from heat. Mixture was partitioned between ethyl acetate and water. Two phases were separated and the aqueous layer was extracted with ethyl acetate. Organic layers were combined, washed with brine, dried over magnesium sulfate, filtered, and evaporated. Residue was purified by silica gel flash chromatography to give 0.1 g (0.3 mmol) of product. 1H NMR (200 MHz, CDCl3) δ 11.89 (s, 1 H), 8.41 (m, 1 H), 8.25 (m, 1 H), 7.84 (m, 2 H), 4.49 (t, J=7.0 Hz, 2 H), 1.87 (m, 2 H), 1.47 (m, 2 H), 1.00 (t, J=7.2 Hz, 3 H).

Workup

customwas removed
temperaturefrom heat
customMixture was partitioned between ethyl acetate and water
customTwo phases were separated
extractionthe aqueous layer was extracted with ethyl acetate
washwashed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customResidue was purified by silica gel flash chromatography

Sources & evidence

ORD record: ord-d373bef4fa3746c49b41800149698d12
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916585B2

Reaction notes

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