Sodium Hydroxide → HCID 19045329, compound

HRID 1781361Notes

Reaction equation

HRID 1781361 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]2([CH2:17][C:16]3[C:11](=[CH:12][C:13]([N+:18]([O-])=O)=[CH:14][CH:15]=3)[C:10]2=[O:21])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(O)(=O)C.Cl.O.[Cl-].[Ti+3].[Cl-].[Cl-]>[C:1]([N:4]1[CH2:5][CH2:6][C:7]2([CH2:17][C:16]3[C:11](=[CH:12][C:13]([NH2:18])=[CH:14][CH:15]=3)[C:10]2=[O:21])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 190455381′-Acetyl-6-nitrospiro[2H-indene-2,4′-piperidin]-1(3H)-one

Product 1

HCID 19045329HCID 19045329, compoundYield 112.3%

Reagents, catalysts & solvents 4

HCID 10313229titanium(III) trichlorideCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 0.29 g (1.0 mmole) 1'-acetyl-1,3-dihydro-6-nitro-1-oxospiro[2H-indene-2,4'-piperidine] in 4 ml acetic acid was added 3.75 ml (4.3 mmoles) of 15% titanium (III) chloride solution in 20-30% aqueous hydrochloric acid dropwise and portionwise over 2 hours. The reaction mixture was made basic (pH 10) with saturated sodium bicarbonate solution and 10N sodium hydroxide solution, diluted with 50 ml water, and extracted with 3×50 ml ethyl acetate. The combined extracts were washed with 20 ml water and brine, dried, and the solvent was removed in vacuo to give 0.29 g crude 1'-acetyl-6-amino-1,3-dihydro-1-oxospiro[2H-indene-2,4'-piperidine].

Workup

  1. extractionextracted with 3×50 ml ethyl acetate
  2. washThe combined extracts were washed with 20 ml water and brine
  3. customdried
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-55054c5686e74d75b17896bf1ce5c7ef
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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