Sodium Hydroxide → HCID 9920694, compound

HRID 720733Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 14000972N-(2-Methylquinolin-8-yl)acetamide

Product 1

HCID 9920694HCID 9920694, compoundYield 57%

Procedure

Reaction of N-(2-methyl-quinol-8-yl)acetamide (159 mg, 0.795 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-8-yl)acetamide (92 mg, 57%): 1H NMR δ 1.57–1.66 (m, 1H), 1.77–1.86 (m, 2H), 2.02 (s, 3H), 2.44 (s, 3H), 2.43–2.57 (m, 1H), 2.68–2.73 (m, 2H), 4.67–4.74 (m, 1H), 6.79 (br s, 1H), 6.92 (d, 1H, J=8 Hz), 7.24 (d, 1H, J=8 Hz); 13C NMR δ 21.6, 25.4, 25.8, 29.6, 31.0, 53.0, 123.4, 131.4, 139.2, 155.9, 157.2, 172.2; MS m/z: 227 (M+Na+). N-(2-Methyl-1,2,3,4-tetrahydroquinolin-8-yl)acetamide also was isolated (25 mg, 15%) as a tautomeric mixture of acyclic and cyclized isomers in an approximately 1:2 ratio which exhibited the following data: 1H NMR δ 1.21–1.25 (m), 1.45–1.61 (m), 1.90 (s), 1.90–1.95 (m), 2.20 (s), 2.71–2.91 (m), 3.32–3.43 (m), 4.00 (br s), 6.56 (dd, J=8, 8 Hz), 6.63 (dd, J=8, 8 Hz), 6.66 (br s), 6.83 (d, J=8 Hz), 6.87 (d, J=8 Hz), 6.94 (d, J=8 Hz), 7.02 (d, J=8 Hz), 7.06 (br s); MS m/z: 205 (M+H+).

Sources & evidence

ORD record: ord-4df472240d8941638fd5a14ba67a32f0
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135570B2

Reaction notes

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