Hydrochloric Acid → HCID 57626218, compound

HRID 2077267Notes

Reaction equation

[CH2:1]([N:6]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][C:8]([C:17]([O:19]CC)=[O:18])=[N:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].O.[OH-].[Li+].Cl>O1CCCC1.C(OCC)C>[CH2:1]([N:6]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][C:8]([C:17]([OH:19])=[O:18])=[N:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 70 °C

Procedure

To a magnetically stirred solution of ethyl 1-(n-pentyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxylate (Intermediate (V-1) (11.76 g, 38.74 mmol) in tetrahydrofuran (100 ml) and water (100 ml) was added lithium hydroxide (1.86 g, 77.5 mmol) and the resulting mixture was heated at 70° C. for 1 hour. The reaction mixture was allowed to attain room temperature and diethyl ether (200 ml) and concentrated hydrochloric acid (7 ml) were added. The organic layer was separated, washed three times with water and with brine and subsequently dried over Na2SO4, filtered and concentrated in vacuo to give 1-(n-pentyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxylic acid (Intermediate (VI-1) (7.9 g, 74% yield) as an oil. 1H-NMR (400 MHz, CDCl3) δ 0.84 (t, J=7, 3H), 1.15-1.28 (m, 4H), 1.53-1.65 (m, 2H), 2.92 (dd, J=17 and 13, 1H), 3.02-3.11 (m, 1H), 3.18-3.27 (m, 1H), 3.44 (dd, J=17 and 13, 1H), 4.75 t, J=13, 1H), 7.31-7.41 (m, 5H), 7.42-9.00 (br s, 1H).

Workup

customto attain room temperature
customThe organic layer was separated
washwashed three times with water
dry with materialwith brine and subsequently dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-dfdb854df12d4705938ef3803bb51b73
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928134B2

Reaction notes

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