Sodium Hydroxide → HCID 9899058, compound

HRID 271807Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12](=[O:14])[CH3:13])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>>[N:1]1[C:10]2[CH2:9][CH:8]([NH:11][C:12](=[O:14])[CH3:13])[CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 37391Acetamide, N-7-quinolyl-

Product 1

HCID 9899058HCID 9899058, compoundYield 25%

Procedure

Reaction of N-(quinol-7-yl)acetamide (33 mg, 0.177 mmol) using the general procedure for small scale hydrogenations (workup with NaOH in place of saturated NaHCO3) provided N-(5,6,7,8-tetrahydroquinolin-7-yl)acetamide (8.3 mg, 25%): 1H NMR □ 1.72-1.83 (m, 1H), 1.99 (s, 3H), 2.04-2.20 (m, 2H), 2.72-2.95 (m, 3H), 3.25 (dd, 1H, J=5, 17 Hz), 4.29-4.40 (m, 1H), 5.72 (br s, 1H), 7.05 (dd, 1H, J=4, 8 Hz), 7.38 (d, 1H, J=8 Hz), 8.35 (d, 1H, J=4 Hz); 13C NMR □ 23.9, 26.5, 28.7, 39.0, 45.6, 121.9, 131.4, 137.0, 147.7, 154.8, 170.1; MS m/z: 213 (M+Na+). N-(1,2,3,4-tetrahydroquinolin-7-yl)acetamide also was isolated (6.5 mg, 20%): 1H NMR □ 1.24-1.28 (s, 1H), 1.87-1.95 (m, 2H), 2.70 (dd, 2H, J=6, 6 Hz), 3.28 (dd, 2H, J=5, 5 Hz), 6.46 (d, 1H, J=8 Hz), 6.84 (d, 1H, J=8 Hz), 6.93 (s, 1H), 7.03 (br s, 1H); 13C NMR□ 22.1, 24.7, 26.6, 37.9, 105.6, 108.3, 117.6, 129.6, 136.5, 145.1, 168.1; MS m/z: 213 (M+Na+).

Sources & evidence

ORD record: ord-88589981796a422d94f4ff567b67ab4c
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452994B2

Reaction notes

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