Sodium Hydroxide → HCID 11084654, compound

HRID 720734Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 588988Acetamide, N-1-isoquinolinyl-

Product 1

HCID 11084654HCID 11084654, compoundYield 59.1%

Procedure

Reaction of N-(isoquinol-1-yl)acetamide (159 mg, 0.854 mmol) using the general procedure for small scale hydrogenations (workup with NaOH in place of saturated NaHCO3) provided N-(5,6,7,8-tetrahydroisoquinolin-1-yl)acetamide (96 mg, 59%): 1H NMR δ 1.74–1.76 (m, 4H), 2.16–2.19 (m, 3H), 2.60–2.70 (m, 2H), 2.70–2.76 (m, 2H), 6.86 (d, 1H, J=5 Hz), 8.03 (d, 1H, J=5 Hz); 13C NMR δ 22.3, 22.8, 23.8, 25.1, 29.6, 122.9, 144.4 (2C), 149.5, 150.2, 170.6; MS m/z: 213 (M+Na+). N-(1,2,3,4-tetrahydroisoquinolin-1-yl)acetamide also was isolated (16 mg, 11%): 1H NMR δ 2.28 (m, 3H), 2.96–3.01 (m, 2H), 3.56–3.61 (m, 2H), 7.20 (d, 1H, J=8 Hz), 7.33–7.38 (m, 1H), 7.44–7.49 (m, 1H), 8.27 (d, 1H, J=8 Hz); 13C NMR δ 27.2, 28.7, 29.7, 39.3, 127.3, 127.5, 128.0, 132.6, 137.9, 162.8, 188.0; MS m/z: 191 (M+H+).

Sources & evidence

ORD record: ord-b564d6b676d14622b16357b333b6e409
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135570B2

Reaction notes

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