Nitric Acid → HCID 86608928, compound

HRID 2112408Notes

Reaction equation

HRID 2112408 reaction equation
[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:17]([O:18][C:19](=[O:22])[CH2:20][CH3:21])[C@H:12]3[O:13][C:14](=[O:16])[CH3:15])[C:4]=2[N:5]=[CH:6][N:7]=1.[N+:30]([O-])([OH:32])=[O:31].S(=O)(=O)(O)O>ClCCl.O>[NH2:1][C:2]1[C:3]2[C:10]([N+:30]([O-:32])=[O:31])=[CH:9][N:8]([C@@H:11]3[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:17]([O:18][C:19](=[O:22])[CH2:20][CH3:21])[C@H:12]3[O:13][C:14](=[O:16])[CH3:15])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 86608927HCID 86608927, compound

Product 1

HCID 86608928HCID 86608928, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the product from Step 4 (1.5 g, 3.69 mmol) in dichloromethane (25 mL) was cooled to 0° C. and a 1:1 mixture of fuming nitric acid and sulfuric acid (4 mL) was added dropwise and the reaction was vigorously stirred at 0° C. for 20 min. The reaction was quenched with ice cold saturated sodium bicarbonate solution. The quenched reaction was diluted with water and extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by plating on silica gel with dichloromethane and eluded by ramping to 5% methanol in dichloromethane to give 600 mg (36%);

Workup

  1. additionwas added dropwise
  2. customThe reaction was quenched with ice cold saturated sodium bicarbonate solution
  3. customThe quenched reaction
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. customto give 600 mg (36%)

Sources & evidence

ORD record
ord-ab33a199a0ef4ef1bd9f634ab8064b31
Source dataset
uspto-grants-2009_04
Patent number
US07524825B2

Reaction notes

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