Hydrazine → HCID 178507272, compound

HRID 928243Notes

Reaction equation

HRID 928243 reaction equation
[C:1]1([C:11]([CH2:13][C:14]#[N:15])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:16][NH2:17]>C(O)C>[C:1]1([C:11]2[CH:13]=[C:14]([NH2:15])[NH:17][N:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 219434673-(Naphthalen-1-yl)-3-oxopropanenitrile

Product 1

HCID 178507272HCID 178507272, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Naphthoylacetonitrile (161 mg, 0.825 mmol) and hydrazine (0.11 mL, 3.5 mmol) are heated in ethanol (1.1 mL) at 70° C. in a sealed vial for 60 hr. The reaction is cooled to room temperature and the solvent is removed. The crude material is taken up in 5 ml of ethyl acetate and washed with water and brine. The organic layer is concentrated in vacuo to give 3-(1-naphthyl)-1H-pyrazol-5-amine which is dissolved in acetic acid (0.375 mL, 6.60 mmol). Diethyl ethoxymethylenemalonate (0.182 mL, 0.907 mmol) is added and the mixture is heated at 120° C. for 3 hr in a sealed vial. During the reaction, a precipitate forms. The reaction is cooled to room temperature and the solid is collected in a Buchner funnel and washed with reagent grade alcohol to provide ethyl 2-(1-naphthyl)-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate (166 mg, yield 60%). 1H NMR (300 MHz, DMSO) δ 8.73-8.66 (m, 1H), 8.64 (s, 1H), 8.02 (dd, J=8.9, 3.4 Hz, 2H), 7.87-7.78 (m, 1H), 7.68-7.52 (m, 3H), 6.71 (s, 1H), 4.25 (q, J=7.1 Hz, 2H), 1.30 (t, J=7.1 Hz, 3H).

Workup

  1. customthe solvent is removed
  2. washwashed with water and brine
  3. concentrationThe organic layer is concentrated in vacuo

Sources & evidence

ORD record
ord-3f6d61194cba4c0a86d08a8b2ff061c0
Source dataset
uspto-grants-2016_03
Patent number
US09290500B2

Reaction notes

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