3-Chloro-1-propyne → Methyl 2-hydroxy-4-propargyloxybenzoate

HRID 1906735

Reaction equation

HRID 1906735 reaction equation
N[C:2]1C(N)=NC=CN=1.C[O:10][C:11]1[CH:19]=[C:18]([O:20][CH2:21][C:22]#[CH:23])[CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].OC1C=C(O)C=CC=1C(OC)=O.C(Cl)C#C>>[OH:10][C:11]1[CH:19]=[C:18]([O:20][CH2:21][C:22]#[CH:23])[CH:17]=[CH:16][C:12]=1[C:13]([O:15][CH3:2])=[O:14]

Participants

5

Reactant 4

HCID 122213-Chloro-1-propyneHCID 16523Methyl 2,4-DihydroxybenzoateHCID 284161Pyrazine-2,3-diamineHCID 131214602-Methoxy-4-[(prop-2-yn-1-yl)oxy]benzoic acid

Product 1

HCID 13121476Methyl 2-hydroxy-4-propargyloxybenzoate

Procedure

A mixture of 11 g of 2,3-diaminopyrazine (IIa), 20.6 g of 2-methoxy-4-propargyloxybenzoic acid [m.p. 142°; obtainable by reacting methyl 2,4-dihydroxybenzoate with propargyl chloride to give methyl 2-hydroxy-4-propargyloxybenzoate (m.p. 100°), reacting the latter with methyl iodide to give methyl 2-methoxy-4-propargyloxybenzoate (m.p. 88°), and hydrolysing the latter] and 300 ml of POCl3 is boiled for 2 hours. The mixture is evaporated to dryness, ice-water is added to the residue, and the mixture is rendered alkaline with K2CO3 solution. The precipitated 2-(2-methoxy-4-propargyloxyphenyl)-1,3,4,7-tetraazaindene is filtered off. M.p. 189°-190°.

Sources & evidence

ORD record
ord-1d0fc1b72c2a41809c4454b901cd30b6
Source dataset
uspto-grants-1987_03
Patent number
US04654344

Linked notes

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