Acetic Anhydride → HCID 59725957, compound

HRID 1912770Notes

Reaction equation

HRID 1912770 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:19])[C:13]=3[CH:12]=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:20](OC(=O)C)(=[O:22])[CH3:21].C(N(CC)CC)C>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:13](=[C:14]([O:19][C:20](=[O:22])[CH3:21])[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 23155162HCID 23155162, compound

Product 1

HCID 59725957HCID 59725957, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 8 mL of methylene chloride, 387 mg (1.52 mmol) of 1-(4-nitrophenyl)-1H-indole-4-ol was dissolved, and 0.186 mL (2.00 mmol) of acetic anhydride and 0.318 mL (2.28 mmol) of triethylamine were added thereto and the mixture solution was stirred at room temperature for 14 hours. The reaction solution was partitioned between methylene chloride (50 mL) and a saturated ammonium chloride aqueous solution (20 mL) and washed with a saturated sodium chloride solution, and the organic layer was dried and then concentrated under reduced pressure to obtain acetic acid 1-(4-nitrophenyl)-1H-indol-4-yl ester. The product was used in the next reaction without further purification.

Workup

  1. customThe reaction solution was partitioned between methylene chloride (50 mL)
  2. washa saturated ammonium chloride aqueous solution (20 mL) and washed with a saturated sodium chloride solution
  3. customthe organic layer was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45b97020bb0e4d08b93e179e170db6f6
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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