Triethylamine → 4-(7-Chloroquinolin-2-ylmethoxy)benzyl chloride

HRID 54531Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:21]=[CH:20][C:17]([CH2:18]O)=[CH:16][CH:15]=3)=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl-].[Li+].CS([Cl:35])(=O)=O>CN(C1C=CN=CC=1)C.CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:21]=[CH:20][C:17]([CH2:18][Cl:35])=[CH:16][CH:15]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -10 °C

Procedure

A mixture of 4-(7-chloroquinolin-2-ylmethoxy)benzyl alcohol (2.80 g, 9.33 mmol), triethylamine (3.12 g, 30.9 mmol), lithium chloride (0.850 g, 20.0 mmol), and 4-(N,N-dimethylamino)pyridine (10 mg) in DMF (40 mL) was cooled to -10° C. Methanesulfonyl chloride (3.40 g, 29.7 mmol) was added dropwise and the resulting mixture was stirred for 15 minutes. The mixture was warmed to room temperature and stirred for an additional 4 hours, then diluted with ethyl acetate. The resulting solution was washed once with water, dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography of the residue (silica gel, ethyl acetate/hexane gradient) provided 1.60 g (54%) of the intermediate.

Workup

temperatureThe mixture was warmed to room temperature
stirringstirred for an additional 4 hours
washThe resulting solution was washed once with water
dry with materialdried (sodium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-25a0764abbd94bc6a51c22e6581de1bc
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05622969

Reaction notes

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