Pyridine → Heptyl-Carbamic Acid quinolin-6-yl ester

HRID 1441925Notes

Reaction equation

HRID 1441925 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:12]([N:19]=[C:20]=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].N1C=CC=CC=1>O1CCCC1>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:20](=[O:21])[NH:19][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 113746-HydroxyquinolineHCID 138341n-Heptyl isocyanate

Product 1

HCID 11558303Heptyl-Carbamic Acid quinolin-6-yl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of quinolin-6-ol (0.29 g., 2 mmol), heptyl isocyanate (0.386 ml 2.4 mmol) and pyridine (1 ml) in dry tetrahydrofuran (10 ml) was heated at 65° C. with stirring for 5 hours. The reaction mixture was cooled and then quenched with water (1 ml), the reaction mixture was concentrated under vaccum and the separated solid was washed with water (2×5 ml) and crystallised with ether to give 1b; yield: 0.25 g. (43.7%), m.p. 78° C., C17H22N2O2; 1H NMR δ ppm (CDCl3): 0.88 (bs, 3H), 1.33-1.34 (m, 8H), 1.57-1.62 (m, 2H), 3.25-3.35 (m, 2H) 5.10 (s, 1H), 7.36-7.52 (m, 1H), 7.47-7.52 (m, 1H), 7.60-7.61 (m, 1H), 8.07-8.12 (m, 2H), 8.86-8.88 (m, 1H), IR vmax (KBr) (cm−1) 478, 648, 731, 771, 838, 910, 977, 1024, 1157, 1215, 1363, 1464, 1498, 1532, 1600, 1719, 2371, 2861, 2944, 3022, 3359, 3762; MS: m/z: 287 (M+).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with water (1 ml)
  3. concentrationthe reaction mixture was concentrated under vaccum
  4. washthe separated solid was washed with water (2×5 ml)
  5. customcrystallised with ether

Sources & evidence

ORD record
ord-90b8c869e1224a7f821d353fdbf4c345
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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