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Hydrochloric Acid → HCID 57626218, compound

HRID 2077267
Notes
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Reaction equation

HRID 2077267 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 57626265HCID 57626265, compound

Product 1

HCID 57626218HCID 57626218, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 3283Diethyl Ether
Solvent
HCID 8028TetrahydrofuranSolvent

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

  1. customto attain room temperature
  2. customThe organic layer was separated
  3. washwashed three times with water
  4. dry with materialwith brine and subsequently dried over Na2SO4
  5. filtrationfiltered
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes