Sodium Hydroxide → HCID 10965308, compound

HRID 720735Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 37481985-ACETAMIDOISOQUINOLINE

Product 1

HCID 10965308HCID 10965308, compoundYield 45.2%

Procedure

Reaction of N-(isoquinol-5-yl)acetamide (171 mg, 0.918 mmol) using the general procedure for small scale hydrogenations (workup with NaOH in place of saturated NaHCO3) provided N-(5,6,7,8-tetrahydroisoquinolin-5-yl)acetamide (79 mg, 45%): 1H NMR δ 1.60–1.70 (m, 1H), 1.70–1.09 (m, 2H), 1.98 (s, 3H), 1.98–2.08 (m, 0.1H), 2.65–2.68 (m, 2H), 5.03–5.11 (m, 1H), 6.63 (br d, 1H), 7.08 (d, 1H, J=5 Hz), 8.17 (s, 1H), 8.20 (d, 1H, J=5 Hz); 13C NMR δ 20.7, 23.7, 26.4, 30.1, 47.1, 122.9, 133.3, 146.3, 147.5, 150.7, 170.1; MS m/z: 191 (M+H+). N-(1,2,3,4-tetrahydroisoquinolin-5-yl)acetamide also was isolated (35 mg, 20%).

Sources & evidence

ORD record: ord-c294de7ad9924377bb89ed853daac14e
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135570B2

Reaction notes

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