Hydroxyamine hydrochloride → 1,10a-Dihydropyrrolo[1,2-b]isoquinoline-3,10[2H,5H]-dione oxime

HRID 652239Notes

Reaction equation

HRID 652239 reaction equation
[CH2:1]1[CH:13]2[N:4]([CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:12]2=[O:14])[C:3](=O)[CH2:2]1.Cl.[NH2:17][OH:18].O.O.O.C([O-])(=O)C.[Na+]>C(O)C.O>[CH2:1]1[CH:13]2[N:4]([CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:12]2=[O:14])[C:3](=[N:17][OH:18])[CH2:2]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 131500811,10a-Dihydropyrrolo[1,2-b]isoquinoline-3,10[2H,5H]-dioneHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 736637961,10a-Dihydropyrrolo[1,2-b]isoquinoline-3,10[2H,5H]-dione oximeYield 81.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture consisting of 2.5 g of 1,10a-dihydropyrrolo[1,2-b]isoquinoline-3,10[2H,5H]-dione in 20 ml of 95% ethanol (EtOH), 1.72 g of hydroxylamine hydrochloride in 10 ml of water and 3.7 g of sodium acetate trihydrate in 10 ml of water was refluxed for 7 hours and thereafter allowed to stand overnight at ambient temperature. The product crystallized from the reaction mixture to give 2.2 g of crystals. Recrystallization from 95% EtOH gave 1.4 g of crystals, m.p. 206°-209° C.

Workup

  1. customThe product crystallized from the reaction mixture

Sources & evidence

ORD record
ord-28bbd5ebfc57458ca3cff4fc0f5eb57d
Source dataset
uspto-grants-1987_06
Patent number
US04670562

Reaction notes

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