Nitric Acid → (cis)-4-(3,4-Diethoxyphenyl)-2-(2-nitroxy-1-ethyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one hydrochloride

HRID 1871382Notes

Reaction equation

HRID 1871382 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=O)[CH3:2].[N+:8]([O-:11])([OH:10])=[O:9].CO[C:14]1[CH:15]=[C:16]([C:22]2[C@H:31]3[C@H:26]([CH2:27][CH2:28][CH2:29][CH2:30]3)[C:25](=[O:32])[N:24]([CH2:33][CH2:34]O)[N:23]=2)C=C[C:19]=1[O:20][CH3:21].O.[Cl:37][CH2:38]Cl>>[ClH:37].[CH2:1]([O:4][C:5]1[CH:6]=[C:16]([C:22]2[C@H:31]3[C@H:26]([CH2:27][CH2:28][CH2:29][CH2:30]3)[C:25](=[O:32])[N:24]([CH2:33][CH2:34][O:9][N+:8]([O-:11])=[O:10])[N:23]=2)[CH:15]=[CH:14][C:19]=1[O:20][CH2:21][CH3:38])[CH3:2]

Participants

6

Reactant 5

HCID 944Nitric AcidHCID 962WaterHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 86755609(cis)-4-(3,4-Dimethoxyphenyl)-2-(2-hydroxy-1-ethyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one

Product 1

HCID 86755607(cis)-4-(3,4-Diethoxyphenyl)-2-(2-nitroxy-1-ethyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one hydrochloride

Procedure

A mixture of 20 mmol of acetic anhydride and 20 mmol of nitric acid was added to a solution of 10 mmol of compound 35 in 100 ml of dichloromethane at 0° C. After 30 min 150 ml of water was added to the mixture and the organic layer dried over magnesium sulfate and evaporated. Crystallisation from ethyl acetate. M.p. 139-140° C.

Workup

  1. dry with materialthe organic layer dried over magnesium sulfate
  2. customevaporated
  3. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-543a6af7534f4aef80091b2d646df41b
Source dataset
uspto-grants-2000_08
Patent number
US06103718

Reaction notes

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