Nitric Acid → HCID 178526430, compound

HRID 1490277Notes

Reaction equation

HRID 1490277 reaction equation
Cl.[CH:2]1[C:18]2[CH:17]=[C:16]3[C:8](=[C:9]4[C:14](=[N:15]3)[CH:13]=[CH:12][CH:11]=[CH:10]4)[NH2+:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[N+:19]([O-:22])([OH:21])=[O:20].CCOC(C)=O.CCCCCC>C(O)(=O)C>[N+:19]([C:10]1[C:9]2[C:14]([CH:13]=[CH:12][CH:11]=1)=[N:15][C:16]1[C:8]=2[NH:7][C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][C:18]=2[CH:17]=1)([O-:21])=[O:20].[N+:19]([C:12]1[CH:11]=[CH:10][C:9]2[C:14]([CH:13]=1)=[N:15][C:16]1[C:8]=2[NH:7][C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][C:18]=2[CH:17]=1)([O-:22])=[O:20]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 21226206Ethyl acetate hexaneHCID 86751463HCID 86751463, compound

Product 2

HCID 178526430HCID 178526430, compoundHCID 178526534HCID 178526534, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of quindolinium hydrochloride [(3.2 g, 1.25 mmol; obtained by acidification of quindoline (example 2) with HCl)], in glacial acetic acid (100 mL) was added dropwise at 0° C. HNO3 (d 1.54, 50 mL). The reaction mixture was stirred at room temperature for 24 hours and poured into ice. The resulting precipitate was collected and washed with a saturated solution of NaHSO4, water and dried to afford 2.4 g 72.5%) of an orange solid. TLC (silica gel, EtOAc-hexane, 1:1) showed two major spots with Rf 0.56 and Rf 0.30. Separation of 1 g of this mixture by LPLC, eluting with EtOAc-hexane (1:3), afforded 290 mg of 6-nitroquindoline (Rf 0.56) and 600 mg of 8-nitroquindoline. The structures of the two compounds were determined by COSY, HMQC, and HMBC 2D-NMR.

Workup

  1. additionpoured into ice
  2. customThe resulting precipitate was collected
  3. washwashed with a saturated solution of NaHSO4, water
  4. customdried
  5. customto afford 2.4 g 72.5%) of an orange solid
  6. customSeparation of 1 g of this mixture by LPLC
  7. washeluting with EtOAc-hexane (1:3)

Sources & evidence

ORD record
ord-3ee31e18ca2547cca963ee5c196311f1
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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