Thionyl Chloride → HCID 68182200, compound

HRID 1620220Notes

Reaction equation

HRID 1620220 reaction equation
[CH2:1]([NH:8][C:9]1[C:18]([CH2:19]O)=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:21][CH3:22])[CH:15]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)[Cl:25]>C(Cl)Cl>[ClH:25].[CH2:1]([NH:8][C:9]1[C:18]([CH2:19][Cl:25])=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:21][CH3:22])[CH:15]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182225HCID 68182225, compound2×

Product 1

HCID 68182200HCID 68182200, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2-(benzylamino)-6-methoxyquinolin-3-yl)methanol SLA 41006 (0.101 g, 0.343 mmol) in dry CH2Cl2 (50 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (0.50 mL, 6.86 mmol). The mixture was stirred for 1 h at RT then concentrated to dryness at 40° C. under vacuum. The residue was then taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give N-benzyl-3-(chloromethyl)-6-methoxyquinolin-2-amine hydrochloride SLA 41008 (120 mg, 100% yield) as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-4ce8a58c241746d5a348b86e0f123c93
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

Loading…