Nitric Acid → HCID 13590788, compound

HRID 542168Notes

Reaction equation

HRID 542168 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][C:5]12[NH:15][C:14](=[O:16])[NH:13][C:12]1=[O:17].[N+:18]([O-])([OH:20])=[O:19]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:18]([O-:20])=[O:19])[CH:11]=1)[NH:8][CH2:7][CH2:6][C:5]12[NH:15][C:14](=[O:16])[NH:13][C:12]1=[O:17]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 12893287HCID 12893287, compound

Product 1

HCID 13590788HCID 13590788, compoundYield 98%

Procedure

5.00 g. (0.0199 mol) of 6'-chloro-1',2',3',4'-tetrahydro-spiro(imidazolidine-5,4'-quinoline)-2,4-dione, formula (V), prepared as described in U.S. Pat. No. 4,235,911, was added to 500 ml of concentrated nitric acid precooled to 7° C. measured internally. After one minute the reaction mixture was poured into 4 liters of ice water and extracted with 2×1 liter of ethyl acetate. The combined organic layers were washed with 1 liter of water, dried over magnesium sulfate, filtered and concentrated to a yellow solid. The solid was slurried in ether/hexane (1/3) filtered and dried in vacuo to provide 5.8 g. (98%) of the title product, m.p. 271° to 274° C. dec.

Workup

  1. customprecooled to 7° C.
  2. extractionextracted with 2×1 liter of ethyl acetate
  3. washThe combined organic layers were washed with 1 liter of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow solid
  7. filtrationfiltered
  8. customdried in vacuo
  9. customto provide 5.8 g

Sources & evidence

ORD record
ord-f0274b7d8dbe4dfcae0e2d9ae1476822
Source dataset
uspto-grants-1987_04
Patent number
US04656169

Reaction notes

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