Nitric Acid → HCID 59620410, compound

HRID 1887769Notes

Reaction equation

HRID 1887769 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(OC(=O)C)(=O)C.S(=O)(=O)(O)O.[O:17]=[C:18]1[CH:27]([NH:28][C:29](=[O:31])[CH3:30])[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19]1.C(OC(C)C)(C)C>C(O)(=O)C>[N+:1]([C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:20]=1[NH:19][C:18](=[O:17])[CH:27]([NH:28][C:29](=[O:31])[CH3:30])[CH2:26]2)([O-:4])=[O:2]

Participants

7

Reactant 5

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 7914Diisopropyl EtherHCID 7918Acetic AnhydrideHCID 44521548HCID 44521548, compound

Product 1

HCID 59620410HCID 59620410, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Fuming nitric acid (2 mL) was added dropwise to acetic anhydride (81 mL) at an internal temperature of 8° C. or lower, and sulfuric acid (81 μL) and a solution of N-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetamide (8.1 g) in acetic acid (81 mL) were sequentially added thereto, followed by stirring at room temperature for 3.5 hours. Diisopropyl ether (162 mL) was added to the mixture, and stirring was performed under cooling on ice for 30 minutes. The formed precipitates were recovered through filtration, washed with diisopropyl ether, and dried under reduced pressure, whereby a mixture of the title compound (A) and N-(8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetamide (B) (A:B=1:1) (7.15 g) was yielded.

Workup

  1. stirringstirring
  2. temperatureunder cooling on ice for 30 minutes
  3. customThe formed precipitates
  4. filtrationwere recovered through filtration
  5. washwashed with diisopropyl ether
  6. customdried under reduced pressure, whereby
  7. additiona mixture of the title compound (A) and N-(8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetamide (B) (A:B=1:1) (7.15 g)
  8. customwas yielded

Sources & evidence

ORD record
ord-c3f3075abdb84194b9b664358ca0aecc
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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