Diazomethane → HCID 54511739, compound

HRID 372846Notes

Reaction equation

HRID 372846 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([OH:19])=[O:18].[N+](=[CH2:22])=[N-]>CCOCC>[CH3:22][O:18][C:17](=[O:19])[CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:3]1[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 14762933PHENYLACETIC ACID,2-(2'-CL-6-ME)ANILINO

Product 1

HCID 54511739HCID 54511739, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 10 g of [o-(3-chloro-o-toluidino)-phenyl]-acetic acid (M.P. 124° - 125°) in 100 ml of ether are slowly added dropwise 100 ml of 2% ethereal diazomethane solution. The solution is allowed to stand for 2 hours at room temperature, and then concentrated to dryness at 40° under 11 Torr. The residue is dissolved in 100 ml of ether. The ether solution is extracted with 40 ml of 2 N sodium hydrogen carbonate solution and water, dried over sodium sulphate, and concentrated at 40° under 11 Torr. The residue is crystallised from benzine. The obtained [o-(3-chloro-o-toluidino)-phenyl]-acetic acid methyl ester melts at 47° - 48°.

Workup

  1. concentrationconcentrated to dryness at 40° under 11 Torr
  2. dissolutionThe residue is dissolved in 100 ml of ether
  3. extractionThe ether solution is extracted with 40 ml of 2 N sodium hydrogen carbonate solution and water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated at 40° under 11 Torr
  6. customThe residue is crystallised from benzine

Sources & evidence

ORD record
ord-e97e6cac5754450297d6a4441d2dcfe6
Source dataset
uspto-grants-1978_05
Patent number
US04092430

Reaction notes

Loading…