Hydrochloric Acid → 3-Chloro-4-(6-hydroxyquinolin-2-yl)benzamide

HRID 1627627Notes

Reaction equation

HRID 1627627 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:21])[CH:17]=2)[N:12]=1)[C:5](O)=[O:6].O=S(Cl)Cl.Cl.[NH4+:27].[OH-]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:21])[CH:17]=2)[N:12]=1)[C:5]([NH2:27])=[O:6]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 56960912Cavosonstat

Product 1

HCID 669800833-Chloro-4-(6-hydroxyquinolin-2-yl)benzamide

Conditions

Temperature
30 °C

Procedure

A mixture of 3-chloro-4-(6-hydroxyquinolin-2-yl)benzoic acid (Compound IV-8, Example 8) (400 mg, 1.33 mmol) and SOCl2 (10 mL) was refluxed for 1 hour, then concentrated under reduced pressure to give crude product (400 mg) as off-white solid. To this solid was added NH4OH (10 mL) and the reaction mixture was stirred at 30° C. for 1 hour. The resulting mixture was acidified with aqueous HCl (2 M) until pH=6 and extracted with EtOAc (50 mL×3), dried over Na2SO4 and concentrated to give crude product (360 mg) as a solid.

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationconcentrated under reduced pressure
  3. customto give crude product (400 mg) as off-white solid
  4. extractionextracted with EtOAc (50 mL×3)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3bd302056c714d7f942554c3ba1707b6
Source dataset
uspto-grants-2014_07
Patent number
US08785643B2

Reaction notes

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