Sodium Hydroxide → HCID 86755205, compound

HRID 1636385Notes

Reaction equation

HRID 1636385 reaction equation
[CH:1]([N:4]1[CH:13]([CH2:14][O:15][NH:16][C:17]([C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=2)=[O:18])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)([CH3:3])[CH3:2].S(Cl)([Cl:30])=O.Cl.[NH2:33][OH:34].C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(Cl)(Cl)Cl.O.O1CCCC1>[ClH:30].[CH:1]([N:4]1[CH:13]([CH2:14][O:15][NH:16][C:17]([C:19]2[CH:27]=[CH:26][C:22]([C:23]([NH:33][OH:34])=[O:24])=[CH:21][CH:20]=2)=[O:18])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 19351083HCID 19351083, compound

Product 1

HCID 86755205HCID 86755205, compoundYield 64.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[(N-isopropyl-1,2,3,4-tetrahydroisoquinol-3-yl)methyloxycarbamoyl]benzoic acid (3.0 g, 7.8 mmol) and thionyl chloride (1.7 ml, 23 mmol) in chloroform (100 ml) was refluxed for 3 hours, then the solvent and thionyl chloride were evaporated. Crude was dissolved in chloroform (100 ml) and evaporated to dryness three times. Crude was dissolved in tetrahydrofuran (50 ml) and added to a solution of hydroxylamine hydrochloride (0.65 g, 9.4 mmol) and sodium bicarbonate (1.3 g, 15.7 mmol) and 1N sodium hydroxide (9.4 ml, 9.4 mmol) in water (30 ml) and tetrahydrofuran (20 ml). The mixture was at room temperature for an hour, then tetrahydrofuran was removed under reduced pressure and the aqueous phase was extracted with ethyl acetate (3×100 ml). The combined organic phases were dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure. Crude was dissolved in tetrahydrofuran and treated with a 1.5 N etheric solution of hydrochloric acid. The solid product was filtered and dried yielding 2.1 g (yield 62%) of pure 4-[(N-isopropyl-1,2,3,4-tetrahydroisoquinol-3-yl)methyloxycarbamoyl]benzohydroxamic acid hydrochloride as white solid. m.p.=154-157° C. (dec.).

Workup

  1. customthe solvent and thionyl chloride were evaporated
  2. dissolutionCrude was dissolved in chloroform (100 ml)
  3. customevaporated to dryness three times
  4. dissolutionCrude was dissolved in tetrahydrofuran (50 ml)
  5. waitThe mixture was at room temperature for an hour
  6. customtetrahydrofuran was removed under reduced pressure
  7. extractionthe aqueous phase was extracted with ethyl acetate (3×100 ml)
  8. dry with materialThe combined organic phases were dried over anhydrous sodium sulphate
  9. customthe solvent was removed under reduced pressure
  10. dissolutionCrude was dissolved in tetrahydrofuran
  11. additiontreated with a 1.5 N etheric solution of hydrochloric acid
  12. filtrationThe solid product was filtered
  13. customdried

Sources & evidence

ORD record
ord-aa7ccfa1366c4b0fb9c107118ce7c44a
Source dataset
uspto-grants-2000_03
Patent number
US06034096

Reaction notes

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