Toluene → HCID 135401118, compound

HRID 456670Notes

Reaction equation

HRID 456670 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[NH:12][C:13]([C:16](=O)[C:17]3[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=3Cl)=[CH:14][CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.ClC1C=CC([N+]([O-])=O)=CC=1CC1NC(C(O)=O)=CC=1.O.[NH2:48][NH2:49].C1(C)C=CC=CC=1>CN1CCCC1=O>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[NH:12][C:13]([C:16]3[C:17]4[C:18](=[CH:19][CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=4)[NH:49][N:48]=3)=[CH:14][CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 24654Hydrazine hydrate (1:1)HCID 18436889HCID 18436889, compoundHCID 86592248HCID 86592248, compound

Product 1

HCID 135401118HCID 135401118, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-(2-chloro-5-nitro-benzoyl)-1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide (250 mg, 0.6 mmol) (made from 5-(2-chloro-5-nitrobenzyl)-1H-pyrrole-2-carboxylic acid using a procedure adapted from that described in Example 32), hydrazine hydrate (0.3 mL), toluene (5 mL) and 1-methyl-pyrrolin-2-one (0.4 mL) was heated at 120° C. for 1.5 hours. The reaction was concentrated, mixed with water and filtered. The solid was washed to give 200 mg of the titled compound as a yellow solid.

Workup

  1. concentrationThe reaction was concentrated
  2. additionmixed with water
  3. filtrationfiltered
  4. washThe solid was washed

Sources & evidence

ORD record
ord-dad2ff996e634df496dd370e0452d01a
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

Loading…