Sodium Carbonate → 2-Amino-2-(2-(heptyloxy)quinolin-6-yl)propan-1-ol

HRID 1802127Notes

Reaction equation

[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+:23]([O-])=O)([CH3:22])[CH2:20][OH:21])[CH:15]=2)[N:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.[Zn]>[NH2:23][C:19]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:18]=[CH:17]2)([CH3:22])[CH2:20][OH:21]

Participants

Conditions

Temperature: 20 °C

Procedure

2-(2-(heptyloxy)quinolin-6-yl)-2-nitropropan-1-ol (200 mg, 0578 mmol) was dissolved in acetic acid (5 mL). zinc (376 mg, 5.78 mmol, 10.0 eq.) was added to the mixture at 0° C. and the mixture was stirred at 20° C. for 15 h. Saturated sodium carbonate solution was added to the mixture until pH=8. Then the mixture was extracted with EtOAc and the organic layer was concentrated and purified by silica gel column chromatography using dichloromethane/methanol (10/1) as eluent to give product (50 mg, 27%) as a slight yellow solid. ESI-MS: 317.2 (M+H)+. HPLC: 95.99%. 1H NMR (400 MHz, CD3OD) δ 8.09 (d, 1H), 7.81-7.79 (m, 2H), 7.68 (q, 1H), 6.92 (d, 1H), 4.38 (t, 2H), 3.84 (d, 1H), 3.74 (d, 1H), 1.86-1.75 (m, 2H), 1.70 (s, 3H), 1.43-1.25 (m, 8H), 0.85 (t, 3H).

Workup

extractionThen the mixture was extracted with EtOAc
concentrationthe organic layer was concentrated
custompurified by silica gel column chromatography

Sources & evidence

ORD record: ord-d528ea821e2d473483b607d2d69f872f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349849B2

Reaction notes

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