Formaldehyde → 2-(2-(Heptyloxy)quinolin-6-yl)-2-nitropropan-1-ol

HRID 709910Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:19]([N+:21]([O-:23])=[O:22])[CH3:20])[CH:15]=2)[N:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C=O.[CH3:26][O:27][Na]>C1COCC1.CO>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]([N+:21]([O-:23])=[O:22])([CH3:20])[CH2:26][OH:27])[CH:15]=2)[N:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

Conditions

Temperature: 80 °C

Procedure

2-(heptyloxy)-6-(1-nitroethyl)quinoline (1.823 g, 5.77 mol) and paraformaldehyde (346 mg, 11.54 mmol, 2.0 eq.) were dissolved in THF (10 mL). CH3ONa (115 mg, 2.13 mmol, 0.37 eq.) in methanol (2 mL) was added to the solution. The mixture was stirred at 80° C. under nitrogen atmosphere for 15 h. The mixture was extracted with ethyl acetate and the organic layer was concentrated and purified by silica gel column chromatography using petroleum/ethyl acetate (5/1) as eluent to give product as a slight red oil (823 mg, 43%). ESI-MS: 347.1 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 1H), 7.88 (d, 1H), 7.69 (d, 1H), 7.56 (q, 1H), 6.93 (d, 1H), 4.62 (d, 1H), 4.47 (t, 2H), 3.90 (d, 1H), 2.15 (s, 3H), 1.84-1.80 (m, 2H), 1.49-1.24 (m, 8H), 0.89 (t, 3H).

Workup

extractionThe mixture was extracted with ethyl acetate
concentrationthe organic layer was concentrated
custompurified by silica gel column chromatography

Sources & evidence

ORD record: ord-e221e2b0dfd04ee8bc0f156ba6aea3d1
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181191B2

Reaction notes

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