Isopropanol → 4-Cyclopropylmethoxy-2-chloromethylpyridine hydrochloride

HRID 1085109Notes

Reaction equation

[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]([CH2:12]O)[CH:7]=2)[CH2:3][CH2:2]1.O=S(Cl)[Cl:16].C(O)(C)C>C(Cl)Cl>[ClH:16].[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]([CH2:12][Cl:16])[CH:7]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

4-cyclopropylmethoxy-2-hydroxymethyl pyridine (93% pure) (0.9 g 0.0046 mol) was dissolved in methylene chloride (10 ml) and cooled to 0° C. SOCl2 (0.5 ml, 0.0069 mol) in methylene chloride (5 ml) was added dropwise at 0° C. and the reaction mixture was stirred 15 min at room temperature. Isopropanol (0.5 ml) was added and the mixture was evaporated giving the desired product (0.68 g, 78%). NMR-data is given below.

Workup

customthe mixture was evaporated

Sources & evidence

ORD record: ord-ec56fb1f617c4b4f968a67e697b533c8
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05008278

Reaction notes

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