Nitric Acid → HCID 22030612, compound

HRID 454309

Reaction equation

HRID 454309 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6]2.[N+:17]([O-])([OH:19])=[O:18]>ClCCl>[OH:2][C:3]1[C:4]([N+:17]([O-:19])=[O:18])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 20926Ethyl 5-methoxyindole-2-carboxylate

Product 1

HCID 22030612HCID 22030612, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 5-methoxyindole-2-carboxylate (8.15 g, 37.2 mmol), (prepared by the method described in Heterocycles Vol. 43, No. 2, p. 263-266), nitric acid adsorbed on silica gel (24 g) and dichloromethane (150 ml) was stirred at ambient temperature for 18 hours. The dichloromethane was removed in vacuo and the product washed off the silica with acetone. The acetone was evaporated in vacuo. The residue was treated again with nitric acid on silica (1 g) as above and the work up procedure repeated to give ethyl 5-hydroxy-4-nitroindole-2-carboxylate (5.8 g, 59%).

Workup

  1. custom(prepared by the method
  2. customThe dichloromethane was removed in vacuo
  3. washthe product washed off the silica with acetone
  4. customThe acetone was evaporated in vacuo
  5. additionThe residue was treated again with nitric acid on silica (1 g) as above and the work up procedure

Sources & evidence

ORD record
ord-132ad3e4bce44edb80e78c38a37e2a70
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Linked notes

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