Nitric Acid → HCID 18367950, compound

HRID 379821Notes

Reaction equation

HRID 379821 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[C:11]([C:15]([OH:17])=[O:16])[NH:12]2)=[CH:8][CH:7]=1>C(OC(=O)C)(=O)C>[Cl:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([N+:1]([O-:4])=[O:2])=[C:11]([C:15]([OH:17])=[O:16])[NH:12]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 855846-Chloro-1H-indole-2-carboxylic acid

Product 1

HCID 18367950HCID 18367950, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled soluton of acetic anhydride (90 ml) and concentrated nitric acid (70%, 10.3 ml) was added 6-chloroindole-2-carboxylic acid (H. W. Ridon and J. C. Tweddle, J. Chem.Soc., 1955, 3499: 18.16 g, 92.84 mmol) portion wise over 20 min. The mixture was stirred for 2 h at 0° C. and the resulting precipitates collected by filtration and washed with a mixture of dichloromethane/hexane (1:1) to give 12.6 g (56%) of the title compound as a yellow solid. 1H-NMR (DMSO-d6) δ: 13.41(1H, br s), 8.04 (1H, d, J=8.8 Hz), 7.62 (1H, d, 1.8 Hz), 7.44 (1H, dd, J=1.8, 8.8 Hz)

Workup

  1. customthe resulting precipitates
  2. filtrationcollected by filtration
  3. washwashed with a mixture of dichloromethane/hexane (1:1)

Sources & evidence

ORD record
ord-13f187a272014e41b4b45c85fe96d7fa
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

Loading…