p-Toluenesulfonic acid monohydrate → HCID 21076642, compound

HRID 1374543Notes

Reaction equation

HRID 1374543 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([CH:12]1[CH2:21][C:20]2[C:15]3=[C:16]([CH2:22][C:23](=[O:24])[N:14]3[CH2:13]1)[CH:17]=[CH:18][CH:19]=2)=[O:11])(=O)C.O.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([CH:12]1[CH2:21][C:20]2[C:15]3=[C:16]([CH2:22][C:23](=[O:24])[N:14]3[CH2:13]1)[CH:17]=[CH:18][CH:19]=2)=[O:11]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21076641HCID 21076641, compound

Product 1

HCID 21076642HCID 21076642, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(6-Acetyloxy-1-oxohexyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one (10.0 g, 30.6 mmol) is suspended in anhydrous ethanol (150 ml), mixed with catalyst amounts of 4-methylbenzenesulfonic acid monohydrate and stirred for five hours at boiling temperature. The solvent volume is concentrated by evaporation to one third, and the product is obtained in the form of light yellow needles (8.22 g, 93.5%) by crystallization at −20° C.

Workup

  1. concentrationThe solvent volume is concentrated by evaporation to one third

Sources & evidence

ORD record
ord-661428b7e9094a9ebf67dd8ee58a1d73
Source dataset
uspto-grants-2007_01
Patent number
US07166588B2

Reaction notes

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