Sodium Hydroxide → HCID 19898931, compound

HRID 1607118Notes

Reaction equation

Cl.[CH3:2][N:3]([CH2:15][CH2:16][N:17]1[N:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]1=[O:27])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1.[OH-].[Na+]>Cl>[NH2:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][N:3]([CH2:15][CH2:16][N:17]2[N:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:27])[CH3:2])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 55 °C

Procedure

Stannous chloride dihydrate (13.05 g) was dissolved in concentrated hydrochloric acid and stirred at 55° C. N-Methyl-N-(4-nitrophenethyl)-2-(2H-phthalazin-1-on-2-yl)ethylamine hydrochloride (7.5 g) was added portionwise over 1 hour and the solution was then heated a further 4 hours at 100° C. The partly cooled solution was poured onto crushed ice containing 500 ml of a 20% aqueous solution of sodium hydroxide and then extracted three times with methylene chloride. The resultant organic extracts were combined, dried (MgSO4), filtered and evaporated to give a pale yellow oil (6.0 g). Chromatography of the oil on silica [Merck "Kieselgel 60" (Trade Mark)] eluting with methylene chloride gave, after collection and evaporation of appropriate fractions, the title compound as a pale yellow oil (3.5 g) which was used in part (C) without further purification.

Workup

temperaturethe solution was then heated a further 4 hours at 100° C
additionThe partly cooled solution was poured
extractionextracted three times with methylene chloride
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-4db2c70eb0204fff993a94781818bdc6
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863948

Reaction notes

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