Oxalyl chloride → 1H-Benz[e]indole-2-carbonyl chloride, 1,1-dimethyl-

HRID 855936Notes

Reaction equation

HRID 855936 reaction equation
[CH3:1][C:2]1([CH3:18])[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7]=[CH:6][C:5]=2[N:4]=[C:3]1[C:15](O)=[O:16].C(Cl)(=O)C([Cl:22])=O>Cl>[CH3:1][C:2]1([CH3:18])[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7]=[CH:6][C:5]=2[N:4]=[C:3]1[C:15]([Cl:22])=[O:16]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 115577531,1-dimethyl-1H-benzo[e]indole-2-carboxylic acid

Product 1

HCID 121368071H-Benz[e]indole-2-carbonyl chloride, 1,1-dimethyl-

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

100 mg 1,1-dimethyl-1H-benzo[e]indole-2-carboxylic acid 3 (see under Example 1) were dissolved in 1.6 mL oxalyl chloride under vigorous developement of HCl-gas. While the solution was stirred at ambient temperature slowly a bright yellow began to precipitate. After 1.5 hours the reaction was complete and the excess of oxalylchloride was removed by distillation to give a yellow solid which was used without further purification.

Workup

  1. customto precipitate
  2. customthe excess of oxalylchloride was removed by distillation
  3. customto give a yellow solid which
  4. customwas used without further purification

Sources & evidence

ORD record
ord-4fee455d644743d5b224239c8ab72ae8
Source dataset
uspto-grants-2007_08
Patent number
US07262306B2

Reaction notes

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