Potassium Carbonate → 5-(5-Aza-spiro[2.4]hept-5-yl)-4-chloro-2-nitro-phenylamine

HRID 1258641Notes

Reaction equation

HRID 1258641 reaction equation
[Cl:1][C:2]1[C:8](Cl)=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[CH2:13]1[C:15]2([CH2:19][CH2:18][NH:17][CH2:16]2)[CH2:14]1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl.CCO>CS(C)=O>[CH2:14]1[C:15]2([CH2:19][CH2:18][N:17]([C:8]3[C:2]([Cl:1])=[CH:3][C:4]([N+:10]([O-:12])=[O:11])=[C:5]([NH2:6])[CH:7]=3)[CH2:16]2)[CH2:13]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 811494,5-Dichloro-2-nitroanilineHCID 21584144Dichloromethane ethanolHCID 219231035-Azaspiro(2.4)heptane

Product 1

HCID 679585435-(5-Aza-spiro[2.4]hept-5-yl)-4-chloro-2-nitro-phenylamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The sub-title compound was prepared from 4,5-dichloro-2-nitroaniline (470 mg, 2.3 mmol), 5-aza-spiro[2.4]heptane (320 mg, 3.3 mmol) and potassium carbonate (470 mg, 3.4 mmol) in DMSO (5 mL) in analogy to example 3, step (a). Yield: 550 mg (91%). Rf(TLC): 0.85 (silica gel, DCM:EtOH 99:1). HPLC-method F: Rf=1.01 min. MS m/z: 533 [2M+H]+.

Sources & evidence

ORD record
ord-093557cfba954537963d9648d837166c
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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