Acetic Acid → 1-Benzyl-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbonitrile

HRID 856960Notes

Reaction equation

[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:19]=O)=[C:15]([OH:18])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[N+:25](CC)([O-])=O.C([O-])(=O)C.[Na+]>O>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:19]#[N:25])=[C:15]([OH:18])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 115 °C

Procedure

To a solution of 1-benzyl-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbaldehyde (45 mg, 0.17 mmol) from step 3 in acetic acid (0.38 mL, 6.6 mmol) was added nitroethane (0.24 mL, 3.4 mmol) and sodium acetate (270 mg, 3.4 mmol). The reaction mixture was heated at a sealed tube at 115° C. overnight. Added some water and extracted it with ether. Combined organic layer and evaporated under vacuum. It was purified by prep TLC eluting with 10% ethyl acetate-hexane and providing 20 mg (45%) of the title compound. 1H-NMR (CDCl3) δ 7.36–7.21 (m, 3H), 7.18–7.14 (m, 2H), 6.99 (s, 1H), 5.98 (s, 1H), 4.48 (s, 2H), 3.41 (t, J=5.7 Hz, 2H), 2.70 (t, J=6.4 Hz, 2H), 1.97 (m, 2H).

Workup

extractionextracted it with ether
customCombined organic layer and evaporated under vacuum
customIt was purified by prep TLC
washeluting with 10% ethyl acetate-hexane

Sources & evidence

ORD record: ord-45f8f82a8e064ea281f92656f36f41df
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144885B2

Reaction notes

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