Water → HCID 178516271, compound

HRID 1370341Notes

Reaction equation

HRID 1370341 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([C:12]([O:14]C)=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:16]1([Li])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>C1COCC1>[C:16]1([C:12]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([OH:1])[CH:11]=2)[OH:14])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 178498588HCID 178498588, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 178516271HCID 178516271, compoundYield 194.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-hydroxy-4-quinolinecarboxylate (406 mg, 2 mmol) in THF (20 mL) at 0° C. was treated with a solution of phenyl lithium (1.8-M in THF, 2.3 mL, 4.2 mmol), stirred at room temperature for 2 h, poured into water (100 mL), the resulting precipitate filtered and dried to give the title compound (636 mg, 97%) as a cream solid: mp>350° C.; IR νmax (Nujol)/cm−1 3550-3300,3085, 3059, 2924, 2854, 1652, 1461, 1377, 759, 750 and 698; NMR δH (400 MHz, ?) 5.66 (1H, s), 6.88 (1H, t, J 7.6 Hz), 7.28-7.39 (11H, m), 7.47 (1H, t, J 7.5 Hz), 7.66 (1H, d, J 8.6 Hz), 7.81 (1H, d, J 7.6 Hz) and 11.63-11.88 (1H, s); M/Z 328 (M+H)+.

Workup

  1. filtrationthe resulting precipitate filtered
  2. customdried

Sources & evidence

ORD record
ord-c649733b938d44129a53f5e8f9637d92
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

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