Sulfuric Acid → Hydrochloric Acid

HRID 1534585Notes

Reaction equation

HRID 1534585 reaction equation
C[O:2][C:3]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)([OH:14])[C:6]2[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:5]=2[CH:4]=1.OS(O)(=O)=O.[OH-].[Na+]>>[Cl:26][C:24]1[CH:23]=[CH:22][C:6]2[C:7]([OH:14])([CH:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[C:8]3=[N:9][CH:10]=[CH:11][CH:12]=[C:13]3[C:3](=[O:2])[CH2:4][C:5]=2[CH:25]=1.[ClH:26]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 14637760HCID 14637760, compound

Product 2

HCID 313Hydrochloric AcidHCID 53853813HCID 53853813, compound

Procedure

Dissolve 5-Methoxy-8-chloro-11-(1-methyl-4-piperidinyl)-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol (4.26 g) in CH30H (6 mL) at 0° C. under an argon atmosphere. Add slowly a cooled solution of 92% aqueous H2SO4 (54 mL). Allow the mixture to warm to room temperature for 35 minutes. Pour the solution onto ice, basify with aqueous NaOH (25%), and extract with methylene chloride (3×). Combine the organic portions, wash with brine and dry over sodium sulfate. Filter and concentrate in vacuo. Triturate the residue with isopropyl ether to give an intermediate, 8-chloro-11-hydroxy-11-(1-methyl-4-piperidinyl)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-5-one as a white solid (3.58 g., 92%, m.p. 170° to 174° C. as HCl salt).

Workup

  1. additionPour the solution onto ice
  2. extractionextract with methylene chloride (3×)
  3. washCombine the organic portions, wash with brine
  4. dry with materialdry over sodium sulfate
  5. filtrationFilter
  6. concentrationconcentrate in vacuo
  7. customTriturate the residue with isopropyl ether

Sources & evidence

ORD record
ord-922264001d7b4d54a711269071df9024
Source dataset
uspto-grants-1992_02
Patent number
US05089496

Reaction notes

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