Thionyl Chloride → HCID 68182244, compound

HRID 1620256Notes

Reaction equation

HRID 1620256 reaction equation
[CH2:1]([NH:3][C:4]1[C:13]([CH2:14]O)=[CH:12][C:11]2[CH:10]=[C:9]3[O:16][CH2:17][O:18][C:8]3=[CH:7][C:6]=2[N:5]=1)[CH3:2].S(Cl)([Cl:21])=O>C(Cl)Cl>[ClH:21].[Cl:21][CH2:14][C:13]1[C:4]([NH:3][CH2:1][CH3:2])=[N:5][C:6]2[CH:7]=[C:8]3[O:18][CH2:17][O:16][C:9]3=[CH:10][C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182189HCID 68182189, compound2×

Product 1

HCID 68182244HCID 68182244, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-(ethylamino)-[1,3]dioxolo[4,5-g]quinolin-7-yl)methanol RBO 40002 (901 mg, 3.66 mmol) in CH2Cl2 (30 mL) in a round-bottomed flask equipped with a magnetic stirrer was added thionyl chloride (2.65 mL, 36.6 mmol). The mixture was stirring for 3 h at RT, evaporated under vacuum at 45° C. and coevaporated twice with CH2Cl2 (to remove SOCl2) to afford 7-(chloromethyl)-N-ethyl-[1,3]dioxolo[4,5-g]quinolin-6-amine hydrochloride RBO 40004 as a yellow solid (1.01 g, 92% yield).

Workup

  1. customevaporated under vacuum at 45° C.

Sources & evidence

ORD record
ord-7d1057edfdbf4195a533ad056cfa158e
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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