Nitric Acid → HCID 67975580, compound

HRID 1844086Notes

Reaction equation

HRID 1844086 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].O.[NH:11]1[C:15](=[O:16])[CH2:14][CH:13]2[CH2:17][C:18]3[C:23]([CH:12]12)=[CH:22][CH:21]=[CH:20][CH:19]=3>[N+](C)([O-])=O>[N+:6]([C:21]1[CH:22]=[C:23]2[C:18]([CH2:17][CH:13]3[CH2:14][C:15](=[O:16])[NH:11][CH:12]32)=[CH:19][CH:20]=1)([O-:9])=[O:7]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962Water2×HCID 1118Sulfuric AcidHCID 67975592HCID 67975592, compound

Product 1

HCID 67975580HCID 67975580, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Sulphuric acid (72 mL) was added to a cooled mixture of nitric acid (63.5 mmol, 4.4 mL) and water (11.3 mL), and the mixture was added dropwise to a cold (2-8° C.) suspension of 3,3a,4,8b-tetrahydro-1H-indeno[1,2-b]pyrrol-2-one (10 g, 57.7 mmol) in nitromethane (100 mL). The mixture was stirred 1.5 h at 2-8° C. after end of addition, and poured onto a mixture of ice and water (1 L). The white suspension was stirred for one hour, filtered and washed with water. The white solid was suspended in 1 L of ethyl acetate, dried and concentrated under vacuum. 7-nitro-3,3a,4,8b-tetrahydro-1H-indeno[1,2-b]pyrrol-2-one (9.2 g, 73%) was obtained. 1H NMR (400 MHz, CD3OD) δ 8.16-8.08 (2H, m), 7.39 (1H, d), 6.89 (1H, brs), 5.09 (1H, d), 3.49-3.37 (2H, m), 2.93 (1H, d), 2.78 (1H, dd), 2.26 (1H, dd) ppm.

Workup

  1. additionafter end of addition
  2. stirringThe white suspension was stirred for one hour
  3. filtrationfiltered
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1c61bbe0154e4b3887e1e1582886a345
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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