Nitric Acid → HCID 15645653, compound

HRID 595835Notes

Reaction equation

HRID 595835 reaction equation
OS(O)(=O)=O.[N+:6]([O-:9])(O)=[O:7].[Br:10][C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:22])[O:19][CH2:20][CH3:21])[CH:14]=[N:15][CH:16]=1>>[Br:10][C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:22])[O:19][CH2:20][CH3:21])[C:14]([N+:6]([O-:9])=[O:7])=[N:15][CH:16]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 2823185HCID 2823185, compound

Product 1

HCID 15645653HCID 15645653, compoundYield 84%

Conditions

Temperature
0 °C

Procedure

To a mixture of concentrated H2SO4 (60 mL, 1126 mmol) and fuming HNO3 (40 mL, 895 mmol), ethyl (5-bromopyridin-3-yl)carbamate (21.5 g, 88 mmol) was added portionwise at 0° C. After stirring at 0° C. for 5 min, the mixture was stirred at rt overnight and poured onto ice water. A crash out formed and was filtered off and washed thoroughly with water and dried. Ethyl (5-bromo-2-nitropyridin-3-yl)carbamate (21.26 g, 84%) was thus obtained as a white solid. LCMS (m/z): 290.1 (MH+), 0.76 min. 1H NMR (400 MHz, CDCl3) δ ppm 9.63 (br. s., 1H) 9.33 (d, J=2.0 Hz, 1H) 8.28 (d, J=2.0 Hz, 1H) 4.32 (q, J=7.3 Hz, 3H) 1.68 (br. s., 2H) 1.38 (t, J=7.0 Hz, 4H).

Workup

  1. additionwas added portionwise at 0° C
  2. stirringthe mixture was stirred at rt overnight
  3. additionpoured onto ice water
  4. customA crash out formed
  5. filtrationwas filtered off
  6. washwashed thoroughly with water
  7. customdried

Sources & evidence

ORD record
ord-54d44a3a25494389bab57abb2f5ed3d1
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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