Thionyl Chloride → HCID 68182136, compound

HRID 1620191Notes

Reaction equation

HRID 1620191 reaction equation
[CH2:1]([NH:3][C:4]1[C:13]([CH2:14]O)=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:16])[CH:10]=2)[N:5]=1)[CH3:2].S(Cl)([Cl:19])=O>C(Cl)Cl>[ClH:19].[Cl:19][CH2:14][C:13]1[C:4]([NH:3][CH2:1][CH3:2])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH3:16])=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182334HCID 68182334, compound2×

Product 1

HCID 68182136HCID 68182136, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-(ethylamino)-6-methylquinolin-3-yl)methanol RBO 35160 (460 mg, 2.13 mmol) in CH2Cl2 (30 mL) in a round-bottomed flask equipped with a magnetic stirrer was added thionyl chloride (1.55 mL, 21.3 mmol). The mixture was stirred for 2 h at RT, evaporated under vacuum at 45° C., coevaporated twice with CH2Cl2 to remove SOCl2 to afford 3-(chloromethyl)-N-ethyl-6-methylquinolin-2-amine hydrochloride RBO 35162 as a yellow solid (520 mg, 90% yield).

Workup

  1. customevaporated under vacuum at 45° C.
  2. customto remove SOCl2

Sources & evidence

ORD record
ord-d4bb866372044a5c803e28f9dc639202
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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