Sodium Hydroxide → HCID 9877694, compound

HRID 271806Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[C:10]([NH:12][C:13](=[O:15])[CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH-].[Na+]>>[CH3:1][C:2]1[CH:11]=[C:10]([NH:12][C:13](=[O:15])[CH3:14])[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 594177Acetamide, N-(2-methyl-4-quinolinyl)-

Product 1

HCID 9877694HCID 9877694, compoundYield 78.6%

Procedure

Reaction of N-(2-methyl-quinolin-4-yl)acetamide (136 mg, 0.679 mmol) using the general procedure for small scale hydrogenations (workup with NaOH in place of saturated NaHCO3) provided N-(2-methyl-5,6,7,8-tetrahydroquinolin-4-yl) acetamide (109 mg, 78%): 1H NMR δ 1.83-1.90 (m, 4H), 2.21 (s, 3H), 2.47 (s, 3H), 2.46-2.2.53 (m, 2H), 2.84-2.87 (m, 2H), 7.18 (br s, 1H), 7.82 (br s, 1H); 13C NMR δ 22.7, 22.8, 23.5, 24.6, 25.3, 33.1, 112.3, 117.3, 143.7, 156.4, 157.3, 169.0; MS m/z: 205 (M+H+).

Sources & evidence

ORD record: ord-19d7740a33f740e59f5b6ca7ae1df20c
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452994B2

Reaction notes

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