Nitric Acid → HCID 131728533, compound

HRID 1695297Notes

Reaction equation

HRID 1695297 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:28])[C:13]2[NH:19][C:18]3[C:20]([Cl:24])=[CH:21][CH:22]=[CH:23][C:17]=3[CH2:16][S:15](=[O:26])(=[O:25])[C:14]=2[CH:27]=1)=[O:9].[N+:29]([O-])([OH:31])=[O:30]>O>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:28])[C:13]2[NH:19][C:18]3[C:20]([Cl:24])=[CH:21][C:22]([N+:29]([O-:31])=[O:30])=[CH:23][C:17]=3[CH2:16][S:15](=[O:25])(=[O:26])[C:14]=2[CH:27]=1)=[O:9]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 131728532HCID 131728532, compound

Product 1

HCID 131728533HCID 131728533, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Cooled sulfuric acid (1 mL) was added to a solution of compound of Example 37e (0.3 g, 0.85 mmol) in concentrated nitric acid (10 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1.5 h. The reaction mixture was slowly poured in cold water (100 mL), solid obtained was filtered, washed with water till pH was neutral. Solid obtained was crystallized using ethyl acetate/pet. ether 60-80° C. to obtain the title compound. Yield: 0.31 g, (91.70%); 1H NMR (DMSO-d6, 300 MHz): δ 2.70 (s, 3H, CH3), 3.90 (s, 3H, OCH3), 5.30 (s, 2H, CH2), 8.10 (s, 1H, Ar), 8.15 (s, 1H, Ar), 8.35 (s, 1H, NH), 8.55 (s, 2H, Ar); MS: m/e (El) 396 (M+).

Workup

  1. customsolid obtained
  2. filtrationwas filtered
  3. washwashed with water till pH
  4. customSolid obtained
  5. customwas crystallized
  6. customethyl acetate/pet. ether 60-80° C.

Sources & evidence

ORD record
ord-d021998bed134d31aacad9939bf1ddcd
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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