Thionyl Chloride → HCID 68182173, compound

HRID 1620272Notes

Reaction equation

HRID 1620272 reaction equation
[CH2:1]([NH:3][C:4]1[C:13]([CH2:14]O)=[CH:12][C:11]2[C:6](=[CH:7][C:8]([F:18])=[C:9]([O:16][CH3:17])[CH:10]=2)[N:5]=1)[CH3:2].O=S(Cl)[Cl:21]>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[C:11]([CH:12]=1)=[CH:10][C:9]([O:16][CH3:17])=[C:8]([F:18])[CH:7]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68182206HCID 68182206, compound2×

Product 1

HCID 68182173HCID 68182173, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-ethylamino-7-fluoro-6-methoxyquinolin-3-yl)methanol SMA 44090 (278 mg, 1.11 mmol) in dry CH2Cl2 (30 mL) at 0° C. under N2 in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (1.60 mL, 22.1 mmol) and the mixture was stirred for 3 h at RT then concentrated to dryness at 40° C. under vacuum. The residue was then diluted with CH2Cl2 (30 mL) and concentrated back to dryness at 40° C. under vacuum (done 3 times) to give 3-(chloromethyl)-N-ethyl-7-fluoro-6-methoxyquinolin-2-amine hydrochloride SMA 44096 as a yellow solid (348 mg, quantitative yield).

Workup

  1. concentrationthen concentrated to dryness at 40° C. under vacuum
  2. additionThe residue was then diluted with CH2Cl2 (30 mL)
  3. concentrationconcentrated back to dryness at 40° C. under vacuum (done 3 times)

Sources & evidence

ORD record
ord-661471e40262439598ea011735990e15
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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