Hydrochloric Acid → HCID 22987158, compound

HRID 2304558Notes

Reaction equation

HRID 2304558 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[F:19])[N:15]=[C:14](Cl)[C:13]([CH:21]=[O:22])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:23].[Na+].Cl>C(#N)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[F:19])[N:15]=[C:14]([I:23])[C:13]([CH:21]=[O:22])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 21891956HCID 21891956, compound

Product 1

HCID 22987158HCID 22987158, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 6-benzyloxy-2-chloro-7-fluoro-3-quinolinecarbaldehyde (obtained according to 1.d, 15 g, 47 mmol) and sodium iodide (18 g, 120 mmol) in anhydrous acetonitrile (500 ml) is treated with a catalytic quantity of concentrated hydrochloric acid (1.2 ml), then taken to reflux under argon for 8 hours. The reaction mixture is then concentrated to 20% of the initial volume, then treated with a 10% aqueous solution of sodium bicarbonate to a neutral pH, then filtered and washed successively with water, ethanol and ethyl ether in order to produce 13 g (68%) of a yellow solid, m.p. 210° C.

Workup

  1. temperatureto reflux under argon for 8 hours
  2. concentrationThe reaction mixture is then concentrated to 20% of the initial volume
  3. additiontreated with a 10% aqueous solution of sodium bicarbonate to a neutral pH
  4. filtrationfiltered
  5. washwashed successively with water, ethanol and ethyl ether in order

Sources & evidence

ORD record
ord-5fc8dae3ce5b4efa92edb806537ff665
Source dataset
uspto-grants-2002_08
Patent number
US06436951B1

Reaction notes

Loading…