4-Chloro-2-toluidine → HCID 2994846, compound

HRID 1786772Notes

Reaction equation

HRID 1786772 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.C(N(CC)C(C)C)(C)C.[C:19]([O:22][C:23]1[C:24](=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:25](Cl)=[O:26])(=[O:21])[CH3:20]>C1(C)C=CC=CC=1>[C:19]([O:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][C:4]=1[CH3:9])=[O:26])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 72514-Chloro-2-toluidineHCID 796682-Acetoxybenzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 2994846HCID 2994846, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 4-chloro-2-methylaniline, 1-1, (10.0 g 0.071 moles) in toluene was added (24.7 mL 0.014 moles) of N,N-diisopropylethylamine, followed by slow addition of acetylsalicyloyl chloride. The mixture was stirred until complete by TLC. Reaction was filtered and dried under vacuum to afford 9.4 grams of 1-2. Analytical LCMS: (CH3CN/H2O/1% TFA, 4 min gradient), 88% pure, M+1 peak m/e 304.

Workup

  1. customReaction
  2. filtrationwas filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-869b7960214f4b0ebb7c5bc8d639ea9d
Source dataset
uspto-grants-2009_03
Patent number
US07507836B2

Reaction notes

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