2-Methyl-5-Nitroaniline → HCID 67494338, compound

HRID 1968928Notes

Reaction equation

HRID 1968928 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4](C=CC(Cl)=O)[CH:3]=1.[CH3:13][C:14]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:15]=1[NH2:16].C(N([CH2:29][CH3:30])CC)C.[C:31](=O)([O-])[O-:32].[K+].[K+]>ClCCl>[CH3:13][C:14]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:15]=1[NH:16][C:31](=[O:32])[CH:29]=[CH:30][C:7]1[CH:6]=[CH:5][CH:4]=[CH:3][N:2]=1

Participants

6

Reactant 4

HCID 74442-Methyl-5-NitroanilineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 713600273-(3-Pyridyl)acryloyl chloride hydrochloride

Product 1

HCID 67494338HCID 67494338, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of the product of step 1 (10.2 g) in anhydrous dichloromethane (250 ml), a solution of 2-methyl-5-nitroaniline (15.2 g) and triethylamine (21 ml, excess allowed) in dichloromethane (60 ml) was added dropwise slowly in an ice-bath with the temperature no more than 5° C. After to addition, the reaction was carried out for 30 min in an ice-bath, and then at room temperature for 3 h. The solution became clear yellow solution. The completion of the reaction was indicated by TLC. After that, potassium carbonate solution (10%) was added, and then the solid was precipitated, and filtered out. The filter cake was washed with water, and dried to give a pale-yellow powdered solid.

Workup

  1. additionAfter to addition
  2. waitat room temperature for 3 h
  3. customthe solid was precipitated
  4. filtrationfiltered out
  5. washThe filter cake was washed with water
  6. customdried
  7. customto give a pale-yellow powdered solid

Sources & evidence

ORD record
ord-8a156a8b1667420ba7e5e4ee89b6a4ed
Source dataset
uspto-grants-2013_04
Patent number
US08426446B2

Reaction notes

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