Water → Hydrochloric Acid

HRID 894389Notes

Reaction equation

HRID 894389 reaction equation
[OH:1][N:2]1[C:11]([CH3:12])=[C:10]([CH2:13][C:14]([O:16]C)=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:18].CC(C)([O-])C.[K+].[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:29]Cl.O.[OH-].[Na+]>O1CCOCC1.C(O)C>[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:29][O:1][N:2]1[C:11]([CH3:12])=[C:10]([CH2:13][C:14]([OH:16])=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:18].[ClH:25]

Participants

9

Reactant 5

HCID 962WaterHCID 76093,4-Dichlorobenzyl chlorideHCID 14798Sodium HydroxideHCID 12715508HCID 12715508, compoundHCID 23665647Potassium tert-butoxide

Product 2

HCID 313Hydrochloric AcidHCID 12715511HCID 12715511, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 1,2-Dihydro-2-hydroxy-3-methyl-1-oxo-4-isoquinoline acetate (0.300 g., 1.21 mmol) suspended in 2 ml. ethanol was reacted with potassium tert-butoxide (0.136 g., 1.21 mmol) (Aldrich). The solid dissolved upon warming. After cooling to room temperature 3,4-dichlorobenzylchloride (0.130 ml., 1.21 mmol) (Pfaltz and Bauer) was added and the mixture was stirred overnight. The residue obtained after vacuum evaporation was taken up in ethyl acetate/hexane and filtered. This mother liquor after evaporation in vacuo gave a solid crude ester (256 mg., 52%, mp 90°-94°) which was hydrolyzed for 24 hr in 6.3 ml. of 5:1 dioxane:water containing 1 equivalent of sodium hyroxide. The title compound was obtained upon acidification with 1 N hydrochloric acid and filtration; 215 mg., 45% overall, mp 222° dec.

Workup

  1. dissolutionThe solid dissolved
  2. temperatureupon warming
  3. additionwas added
  4. customThe residue obtained
  5. customafter vacuum evaporation
  6. filtrationfiltered
  7. customThis mother liquor after evaporation in vacuo
  8. customgave a solid crude ester (256 mg., 52%, mp 90°-94°) which
  9. waitwas hydrolyzed for 24 hr in 6.3 ml

Sources & evidence

ORD record
ord-d3825af93bed4534af3ccb1460b31bd6
Source dataset
uspto-grants-1981_08
Patent number
US04283539

Reaction notes

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