Nitric Acid → HCID 10683434, compound

HRID 1781052Notes

Reaction equation

HRID 1781052 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][CH3:13])[NH:8][C:7](=[O:14])[CH2:6][NH:5]2.[N+:15]([O-])([OH:17])=[O:16].C1OC2C=C3C(NC(=O)C(=O)N3)=CC=2[O:20]1.C(C1C(CC)=CC=CC=1N)C>C(C(O)=O)(F)(F)F>[Cl:1][C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][CH3:13])[NH:8][C:7](=[O:14])[C:6](=[O:20])[NH:5]2

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 10703695HCID 10703695, compoundHCID 10845927HCID 10845927, compound2×HCID 18362470HCID 18362470, compound

Product 1

HCID 10683434HCID 10683434, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 137 mg (0.65 mmol) of 36 in 4 mL of CF3CO2H kept in an ice bath was added dropwise 0.4 mL of fuming HNO3. The solution was stirred in the ice bath for 1 h and at room temperature overnight. It was evaporated and the residue was treated with 6 mL of water and stirred for 10 min. The mixture was filtered, washed with water, and dried to leave a yellow solid, 140 mg (80%); mp>330° C.; 1H NMR (DMSO-d6), 1.161 (t, 3, J=7.4), 2.712 (q, 2, J=7.6), 7.192 (s, 1), 12.209 (mb 2). MS, 269 (M+, 100), 254 (12), 226 (15), 160 (20). HRMS, Cacld for C10H8ClN3O4 269.0198; Found 269.0196.

Workup

  1. customIt was evaporated
  2. additionthe residue was treated with 6 mL of water
  3. filtrationThe mixture was filtered
  4. washwashed with water
  5. customdried
  6. customto leave a yellow solid, 140 mg (80%)

Sources & evidence

ORD record
ord-7dce83d20adb454489999b231737edc2
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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