Phosphorus oxychloride → HCID 85916602, compound

HRID 1395225Notes

Reaction equation

[CH2:1]([N:3]1[C:7]2[N:8]=[CH:9][C:10]3[C:11](=O)[NH:12][C:13]4[N:14]([N:16]=[CH:17][C:18]=4[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:15]=3[C:6]=2[CH:5]=[N:4]1)[CH3:2].P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:11]1[C:10]2[CH:9]=[N:8][C:7]3[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][C:6]=3[C:15]=2[N:14]2[N:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:13]2[N:12]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride2×

HCID 136398824HCID 136398824, compound

Product 1

HCID 85916602HCID 85916602, compound

Procedure

256 g of 8-ethyl-5,8-dihydro-5-oxo-4H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine-3-carboxylic acid, ethyl ester are refluxed in 1 liter of phosphorus oxychloride for 24 hours. The excess phosphorus oxychloride is decomposed by pouring the solution on ice and the crystallized 5-chloro-8-ethyl-8H-pyrazolo[1,5-a]pyrazolo[4', 3':5,6]pyrido[3,4-e]pyrimidine-3-carboxylic acid, ethyl ester is filtered off, yield 245 g (91%); m.p. 170°-172° (butyl alcohol).

Workup

additionby pouring the solution on ice
filtrationthe crystallized 5-chloro-8-ethyl-8H-pyrazolo[1,5-a]pyrazolo[4', 3':5,6]pyrido[3,4-e]pyrimidine-3-carboxylic acid, ethyl ester is filtered off

Sources & evidence

ORD record: ord-83a246de11594a1a8b48376b219c1c72
Source dataset: uspto-grants-1980_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04202899

Reaction notes

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