Thionyl Chloride → HCID 68182129, compound

HRID 1620249Notes

Reaction equation

HRID 1620249 reaction equation
[CH3:1][NH:2][C:3]1[C:12]([CH2:13]O)=[CH:11][C:10]2[CH:9]=[C:8]3[O:15][CH2:16][O:17][C:7]3=[CH:6][C:5]=2[N:4]=1.O=S(Cl)[Cl:20]>C(Cl)Cl>[ClH:20].[Cl:20][CH2:13][C:12]1[C:3]([NH:2][CH3:1])=[N:4][C:5]2[CH:6]=[C:7]3[O:17][CH2:16][O:15][C:8]3=[CH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182265HCID 68182265, compound

Product 1

HCID 68182129HCID 68182129, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (6-(methylamino)-[1,3]dioxolo[4,5-g]quinolin-7-yl)methanol CCH 34158-2 (1.00 g, 4.31 mmol) in dry CH2Cl2 (20 mL) in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (5.0 mL, 68.9 mmol). The mixture was stirred for 2 h at RT then concentrated to dryness at 40° C. under vacuum. The residue was then taken up in CH2Cl2 (15 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give 7-(chloromethyl)-N-methyl-[1,3]dioxolo[4,5-g]quinolin-6-amine hydrochloride CCH 34158B as a yellow solid (1.24 g, 100% yield).

Workup

  1. concentrationthen concentrated to dryness at 40° C. under vacuum
  2. concentrationThe residue was then taken up in CH2Cl2 (15 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times)

Sources & evidence

ORD record
ord-ea1362569b6a4b2e94e4b838f22421b7
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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