2,3-Diaminopyridine → Methyl 2-hydroxy-4-propargyloxybenzoate

HRID 2290406Notes

Reaction equation

HRID 2290406 reaction equation
N[C:2]1C(N)=CC=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 99562,3-DiaminopyridineHCID 122213-Chloro-1-propyneHCID 16523Methyl 2,4-DihydroxybenzoateHCID 131214602-Methoxy-4-[(prop-2-yn-1-yl)oxy]benzoic acid

Product 1

HCID 13121476Methyl 2-hydroxy-4-propargyloxybenzoate

Procedure

A mixture of 10.9 g of 2,3-diaminopyridine (IIa) and 20.6 g of 2-methoxy-4-propargyloxybenzoic acid (m.p.142°; obtainable by the reaction of methyl 2,4-dihydroxybenzoate with propargyl chloride to give methyl 2-hydroxy-4-propargyloxybenzoate (m.p. 100°); reaction of this with methyl iodide to give methyl 2-methoxy-4-propargyloxybenzoate (m.p. 88°) and hydrolysis) is added in portions with stirring to 500 ml of POCl3. The mixture is boiled for 4 hours, concentrated, and the residue is treated with 375 ml of 10% hydrochloric acid. The precipitated 2-(2-methoxy-4-propargyloxyphenyl)imidazo(4,5-b)pyridine hydrochloride ("M") is filtered off. M.p. 247° (from methanol).

Sources & evidence

ORD record
ord-6237f9d6d39642688b70fb88858944df
Source dataset
uspto-grants-1986_10
Patent number
US04616090

Reaction notes

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