Hydrochloric Acid → HCID 86596673, compound

HRID 451617

Reaction equation

HRID 451617 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[N:15](OCCC(C)C)=[O:16].Cl>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[C:9](=[N:15][OH:16])[CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 110305765-Tert-butyl-2,3-dihydroinden-1-one

Product 1

HCID 86596673HCID 86596673, compoundYield 137.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-tert-butyl-indan-1-one (9.39 g, 39 mmol) was dissolved in 150 ml methanol. Isoamyl nitrite (5 g, 43 mmol) and conc. HCl (5 ml) were added, and the reaction stirred at ambient temperature for 44 hours. The solvents were removed under vacuum to give 11.67 grams of crude product which was used without further purification. 1H NMR (300 MHz, CDCl3) 7.82 (d, 1H), 7.51 (s, 1H), 7.49 (d, 1H), 3.83 (s, 2H), 3.50 (s, 1H, OH) 1.34 (s, 9H). MS (CSI) m/e 218 (M+H)+, 235 (m+NH4)+

Workup

  1. customThe solvents were removed under vacuum

Sources & evidence

ORD record
ord-33f1e9d4c2fa409d9d3d76d67b539f6d
Source dataset
uspto-grants-2013_07
Patent number
US08487116B2

Linked notes

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