Hydrochloric Acid → HCID 69158906, compound

HRID 1660988Notes

Reaction equation

HRID 1660988 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:11]([O:13][C:14]([CH:16]1[C:24]2[C:19](=[CH:20][C:21]([NH2:25])=[CH:22][CH:23]=2)[C:18](=[O:26])[CH2:17]1)=[O:15])[CH3:12].Cl>C(O)C.O1CCOCC1>[CH2:11]([O:13][C:14]([CH:16]1[C:24]2[C:19](=[CH:20][C:21]([NH:25][C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=3)=[CH:22][CH:23]=2)[C:18](=[O:26])[CH2:17]1)=[O:15])[CH3:12]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 796132-Chloro-3-nitropyridineHCID 86008622HCID 86008622, compound

Product 1

HCID 69158906HCID 69158906, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 2-chloro-3-nitropyridine (1.48 g, 9.03 mmol), (R/S)-5-Amino-3-oxo-indan-1-carboxylic acid ethyl ester (1.98 g, 9.03 mmol) and 4M HCl in dioxane (2.3 mL, 9.0 mmol) in ethanol (15 mL) is refluxed for 9 h. The reaction mixture is left at rt overnight then a further equivalent of 4M HCl in dioxan is added. After 4 h refluxing, the solvent is evaporated and the crude mixture purified by MPLC eluting with EtOAc/Hexane to give (R/S)-5-(3-Nitro-pyridin-2-ylamino)-3-oxo-indan-1-carboxylic acid ethyl ester as a red solid. Title compound: ES-MS: 342.19 [M+H]+, tR=1.6 min (System 2)

Workup

  1. temperatureis refluxed for 9 h
  2. temperatureAfter 4 h refluxing
  3. customthe solvent is evaporated
  4. customthe crude mixture purified by MPLC
  5. washeluting with EtOAc/Hexane

Sources & evidence

ORD record
ord-760e7ae16a0c4fefb513683873e5efcd
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

Loading…