Sodium Hydroxide → HCID 19045409, compound

HRID 1781385Notes

Reaction equation

HRID 1781385 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[O:28][C:12]3([CH2:17][CH2:16][N:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=4)[CH2:14][CH2:13]3)[CH2:11][C:10](=O)[C:9]=2[CH:30]=1)(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(O)(=O)C.[Cl-].[Ti+3].[Cl-].[Cl-]>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[O:28][C:12]3([CH2:13][CH2:14][N:15]([CH2:18][C:19]4[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=4)[CH2:16][CH2:17]3)[CH2:11][CH2:10][C:9]=2[CH:30]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 19045334HCID 19045334, compound

Product 1

HCID 19045409HCID 19045409, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3,4-dihydro-6-acetamido-1'-(4-nitrobenzyl)spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one (0.58 g, 1.4 mmol) in acetic acid (6.4 ml) was added titanium (III) chloride (15% wt. in 20-30% wt. hydrochloric acid, 7 ml) dropwise. The reaction mixture was stirred at room temperature for 1 hr, cooled to 0° C. and basified with saturated sodium bicarbonate and 20% sodium hydroxide solutions. Extraction with ethyl acetate, drying and solvent evaporation gave an oil (0.42 g). Chromatography (silica gel, chloroform-methanol-ammonium hydroxide, 95/2/0.5) gave 3,4-dihydro-6-acetamido-1'-(4-aminobenzyl)spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one (136 mg, 26%);

Workup

  1. extractionExtraction with ethyl acetate
  2. customdrying
  3. customsolvent evaporation

Sources & evidence

ORD record
ord-9b03d7f6f2964e45a150ed7ab18aa7c8
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

Loading…