Nitric Acid → HCID 67271496, compound

HRID 1696518Notes

Reaction equation

HRID 1696518 reaction equation
[CH2:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:3](=[O:4])[CH2:2]1.O.[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[N+:13]([C:8]1[CH:7]=[C:1]2[C:11](=[CH:10][CH:9]=1)[CH2:6][NH:5][C:3](=[O:4])[CH2:2]2)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 64796Hydrocarbostyril

Product 1

HCID 67271496HCID 67271496, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of hydrocarbostyril (9.00 g, 61.2 mmol) in conc. H2SO4 (180 mL) cooled to −10° C. was slowly added H2O (45 mL), followed by HNO3 (65%, 4.5 mL). The yellow solution was stirred at −10° C. for 10 min and then carefully quenched at −10° C. with H2O (500 mL). The precipitated yellow solid was filtered off, washed with H2O and dried in vacuo to yield 1,2-dihydro-6-nitroisoquinolin-3(4H)-one (10.3 g, 88% yield). 1H NMR (400 MHz, CDCl3): δ 9.35 (brs, 1H), 8.12-8.09 (m, 2H), 6.95-6.92 (m, 1H), 3.10 (t, J=7.6 Hz, 2H), 2.73 (t, J=7.8 Hz, 2H); MS (ESI) m/z: 193.0 (M+H+).

Workup

  1. customcarefully quenched at −10° C. with H2O (500 mL)
  2. filtrationThe precipitated yellow solid was filtered off
  3. washwashed with H2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-58bd0f57983f41ec807afd2bff2b356e
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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