Ethanol → HCID 178524785, compound

HRID 928244Notes

Reaction equation

HRID 928244 reaction equation
[C:1]1([C:11]2[CH:25]=[C:14]3[NH:15][CH:16]=[C:17]([C:20]([O:22]CC)=[O:21])[C:18](=[O:19])[N:13]3[N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(O)C.[Cl-].[NH4+]>[OH-].[Na+].O>[C:1]1([C:11]2[CH:25]=[C:14]3[NH:15][CH:16]=[C:17]([C:20]([OH:22])=[O:21])[C:18](=[O:19])[N:13]3[N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 178469874HCID 178469874, compound

Product 1

HCID 178524785HCID 178524785, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 2-(1-naphthyl)-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate (163 mg, 0.489 mmol) is stirred in 4 M NaOH (2.4 mL) and ethanol (1.2 mL) at 100° C. in a sealed vial for 5 hr during which time a precipitate forms. The reaction mixture is diluted with water and a saturated solution of ammonium chloride to bring the pH to about 4. The precipitate is collected in a Buchner funnel to provide 2-(1-naphthyl)-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid (145 mg, yield 97%). 1H NMR (400 MHz, DMSO) δ 8.74 (s, 1H), 8.72-8.64 (m, 1H), 8.03 (dd, J=11.4, 5.4 Hz, 2H), 7.86 (d, J=6.3 Hz, 1H), 7.69-7.52 (m, 3H), 6.80 (s, 1H).

Workup

  1. customThe precipitate is collected in a Buchner funnel

Sources & evidence

ORD record
ord-d84a9559cbfd4c8eb79e15460d76717c
Source dataset
uspto-grants-2016_03
Patent number
US09290500B2

Reaction notes

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