Nitric Acid → HCID 15230214, compound

HRID 2051031Notes

Reaction equation

HRID 2051031 reaction equation
[Br:1][C:2]1[C:13]([CH3:14])=[CH:12][C:5]2[N:6]3[CH2:11][CH2:10][CH2:9][C:7]3=[N:8][C:4]=2[CH:3]=1.[N+:15]([O-])([OH:17])=[O:16].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[K+].[Br-]>C(Cl)(Cl)Cl.CO>[Br:1][C:2]1[C:13]([CH3:14])=[CH:12][C:5]2[N:6]3[CH2:11][CH2:10][CH2:9][C:7]3=[N:8][C:4]=2[C:3]=1[N+:15]([O-:17])=[O:16]

Participants

7

Reactant 5

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 15661170HCID 15661170, compound

Product 1

HCID 15230214HCID 15230214, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A solution of 245 mg (0.97 mmol) of 23 in a 5 mL mixture of fuming nitric acid and concentrated sulphuric acid (4:1) was stirred in an ice bath for 10 min. The completed reaction was poured over cracked ice and the pH of resulting solution adjusted to 6.5 with aqueous sodium bicarbonate. Extraction of this solution with 3×50 mL portions of chloroform, drying the extracts (sodium sulfate), and then concentration afforded a yellow solid, 165 mg (57%). Recrystallization from chloroform/hexane afforded analytically pure material: mp 201°-203° C.; TLC (chloroform/methanol, [95:5]) Rf =0.61; IR(KBr pellet) 1537, 1517, 1449, 1413, 1383, 1374, 1342, 1297, 884, 860 cm-1 ; 1H NMR (dimethyl sulfoxide-d6) δ7.77 (1 H, s, aromatic proton), 4.15 (2 H, t, J~Hz, C(1) methylene), 2.99 (2 H, t, J~7 Hz, C(3) methylene), 2.67 (2 H, quintet, J~7 Hz, C(2) methylene); 2.52 (3 H, s, 7-methyl); mass spectrum (EI mode) m/z 295 and 297 (P+, 79Br and 81Br), 249 and 251 (P+ -NO2) Anal. Calcd for C11H10BrN3O2 : C, 44.60; H, 3.40; N, 14.18. Found: C, 44.83; H, 3.31; N, 14.07.

Workup

  1. customThe completed reaction
  2. additionwas poured over cracked ice
  3. extractionExtraction of this solution with 3×50 mL portions of chloroform
  4. dry with materialdrying the extracts (sodium sulfate)
  5. concentrationconcentration
  6. customafforded a yellow solid, 165 mg (57%)
  7. customRecrystallization from chloroform/hexane
  8. customafforded analytically pure material

Sources & evidence

ORD record
ord-a73a6ca4d8fd43428ecb922a7eaf0893
Source dataset
uspto-grants-1991_05
Patent number
US05015742

Reaction notes

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