N,N-Diethylaniline → 2,3-dihydropyrano[3,2-e]isoindol-1(7H)-one

HRID 1727398Notes

Reaction equation

HRID 1727398 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][NH:10][C:11]2=[O:14])=[CH:7][CH:6]=1)[C:2]#[CH:3].C(N(CC)C1C=CC=CC=1)C>CCCCCC.CCOC(C)=O.C(Cl)Cl>[C:11]1(=[O:14])[C:12]2[C:13]3[CH:3]=[CH:2][CH2:1][O:4][C:5]=3[CH:6]=[CH:7][C:8]=2[CH2:9][NH:10]1

Participants

4

Reactant 2

HCID 7061N,N-DiethylanilineHCID 575676686-(Prop-2-ynyloxy)isoindolin-1-one

Product 1

HCID 575676832,3-dihydropyrano[3,2-e]isoindol-1(7H)-oneYield 64%

Reagents, catalysts & solvents 1

HCID 21942482Ethyl acetate hexane methylene-chlorideSolvent

Conditions

Temperature
210 °C

Procedure

The mixture of 6-(prop-2-ynyloxy)isoindolin-1-one ((72), 4.4 g, 23.5 mmol) and N,N-Diethylaniline 70 ml) was stirred at 210° C. for overnight. Reaction solution was directly loaded on silica gel eluting with Hexane/EtOAc/CH2Cl2 (3:3:1 ratio) to give the title compound (2.8 g, 64%) as a brown solid. MS (ES) m/z 188.1.

Workup

  1. customReaction solution

Sources & evidence

ORD record
ord-2f8e0f3584f44a8e80967ed562f00b55
Source dataset
uspto-grants-2009_02
Patent number
US07495111B2

Reaction notes

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