Hydroxyamine hydrochloride → 5-(4-chlorophenyl)-3-(hydroxyamino)-8-methyl-7,9-dihydro-6H-pyrrolo[3,2-h]isoquinolin-2-one;hydrochloride

HRID 736441Notes

Reaction equation

HRID 736441 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH2:10][CH2:11][N:12]([CH3:23])[CH2:13][C:14]=3[C:15]3[NH:20][C:19](=[O:21])[C:18](=O)[C:16]=3[CH:17]=2)=[CH:4][CH:3]=1.Cl.[NH2:25][OH:26]>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH2:10][CH2:11][N:12]([CH3:23])[CH2:13][C:14]=3[C:15]3[NH:20][C:19](=[O:21])[C:18](=[N:25][OH:26])[C:16]=3[CH:17]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 543253028-methyl-5-(4-chlorophenyl)-6,7,8,9-tetrahydro-1H-pyrrolo[3,2-h]isoquinoline-2,3-dione

Product 1

HCID 1784800075-(4-chlorophenyl)-3-(hydroxyamino)-8-methyl-7,9-dihydro-6H-pyrrolo[3,2-h]isoquinolin-2-one;hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(4-chlorophenyl)-8-methyl-6,7,8,9-tetrahydro-1-H-pyrrolo[3.2-h]isoquinoline-2,3-dione (0.50 g, 1.53 mmol), hydroxylamine hydrochloride (0.5 g, 7.2 mmol) and ethanol (5 ml, 96%) was stirred at room-temperature for 15 minutes. The colour shifted from yellow to red and the product precipitated. The product was filtered and 0.44 g (76%) was isolated. Mp decomp. 300-305° C.

Workup

  1. customprecipitated
  2. filtrationThe product was filtered
  3. custom0.44 g (76%) was isolated
  4. custom300-305° C.

Sources & evidence

ORD record
ord-2dbc1b03d6fa4ba1a19b83a71688d302
Source dataset
uspto-grants-2009_09
Patent number
US07595336B2

Reaction notes

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