Nitrobenzene → HCID 22452747, compound

HRID 1003232Notes

Reaction equation

HRID 1003232 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[C:15]([S:38][C:10]=2[CH2:9]1)=[N:16][C:17]([CH2:31][N:32]1[CH2:36][CH2:35][CH2:34][C:33]1=[O:37])=[C:18]([Cl:30])[C:19]=3[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)C1C=CC=CC=1.[N+](C1C=CC=CC=1)([O-])=O>[Pd].C1(C)C(C)=CC=CC=1>[Cl:30][C:18]1[C:19]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)=[C:14]2[C:11]3[C:10](=[CH:9][N:8]=[CH:13][CH:12]=3)[S:38][C:15]2=[N:16][C:17]=1[CH2:31][N:32]1[CH2:36][CH2:35][CH2:34][C:33]1=[O:37]

Participants

5

Reactant 2

HCID 7416NitrobenzeneHCID 22452743HCID 22452743, compound

Product 1

HCID 22452747HCID 22452747, compoundYield 10.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of the compound obtained in Example 28B (3.0 g), palladium on carbon (5%, 5.0 g), nitrobenzene (1.3 g) and xylene (100 ml) was stirred under reflux for 4 hours and the insoluble solid was filtered off. The filtrate was concentrated in vacuo and the residue was chromatographed on SiO2 with ethyl acetate to give 3-chloro-4-(3,4-dimethoxyphenyl)-2-(2-oxopyrrolidin-1-ylmethyl)thieno[2,3-b:5,4-c']dipyridine (0.25 g, 10%) as crystals. Recrystallization from ethyl acetate-hexane give colorless prisms, m.p. 228-230° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. filtrationthe insoluble solid was filtered off
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was chromatographed on SiO2 with ethyl acetate

Sources & evidence

ORD record
ord-e88b7eabcaca48cb8b5dbe6b06d2b9be
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

Loading…