Hydrochloric Acid → 6-Bromo-1,2-dihydrospiro[indole-3,4'-oxane]-2-one

HRID 2096960Notes

Reaction equation

HRID 2096960 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]2[N:8](C(OC(C)(C)C)=O)[C:9](=[O:16])[C:10]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.Cl>O1CCOCC1>[Br:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:16])[C:10]3([CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58154281HCID 58154281, compound

Product 1

HCID 669534896-Bromo-1,2-dihydrospiro[indole-3,4'-oxane]-2-oneYield 103.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl 6-bromo-2-oxo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-1-carboxylate (preparation 6b, 4.20 g, 11.0 mmol) and a 5M solution of hydrogen chloride in 1,4-dioxane (25 mL) was stirred at room temperature. After 5 hours, the mixture was concentrated in vacuo to give the title compound (3.20 g, 98%) as a pale pink solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-7b839075c1ac4acba1c3ccfc16be93b5
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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