Thionyl Chloride → HCID 68182263, compound

HRID 1620301Notes

Reaction equation

HRID 1620301 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[F:14])[N:10]=[C:9]([NH:15][CH2:16][CH3:17])[C:8]([CH2:18]O)=[CH:7]2)[CH3:2].O=S(Cl)[Cl:22]>C(Cl)Cl>[ClH:22].[Cl:22][CH2:18][C:8]1[C:9]([NH:15][CH2:16][CH3:17])=[N:10][C:11]2[C:6]([CH:7]=1)=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[C:13]([F:14])[CH:12]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182168HCID 68182168, compound2×

Product 1

HCID 68182263HCID 68182263, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-ethoxy-2-(ethylamino)-7-fluoroquinolin-3-yl)methanol SMA 44104 (61 mg, 0.23 mmol) in dry CH2Cl2 (10 mL) at 0° C. under N2 in a 25 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (0.33 mL, 4.56 mmol) and the mixture was stirred for 3 h at RT. The mixture was then concentrated to dryness at 40° C. under vacuum and the residue was taken up in CH2Cl2 (20 mL) before concentration back to dryness (done 3 times) to give 3-(chloromethyl)-6-ethoxy-N-ethyl-7-fluoroquinolin-2-amine hydrochloride SMA 44106 as a brown solid (88 mg, >100% yield).

Workup

  1. concentrationThe mixture was then concentrated to dryness at 40° C. under vacuum
  2. concentrationthe residue was taken up in CH2Cl2 (20 mL) before concentration back to dryness (done 3 times)

Sources & evidence

ORD record
ord-bbd035157faa40bbadf12949ab129565
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

Loading…