Acetic Anhydride → HCID 20272390, compound

HRID 484802Notes

Reaction equation

HRID 484802 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20])[NH2:6].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:11]1(=[O:20])[N:10]([C:9]2[CH:8]=[CH:7][C:5]([NH:6][C:21](=[O:23])[CH3:22])=[CH:4][C:3]=2[CH3:2])[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]12

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 131714297HCID 131714297, compound

Product 1

HCID 20272390HCID 20272390, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product aniline of Example 31 was acetylated at room temperature using 8.2 ml (86.6 mmole) of acetic anhydride in 100 ml of pyridine. After one day the mixture was concentrated in vacuo to a syrup which afforded a solid upon trituration with water. The solid was collected, washed with water, and dried under vacuum at 40°, giving 4.8 g (16.3 mmole) of 2-phthalimido-5-acetamidotoluene. The intermediate compound was heated at reflux in 100 ml of ethanol containing 3.2 ml (65.2 mmole) of hydrazine hydrate. After 45 minutes the mixture was filtered and the filtrate was concentrated to dryness. The crude amine was used in subsequent reactions without further purification.

Workup

  1. customwas acetylated at room temperature
  2. concentrationAfter one day the mixture was concentrated in vacuo to a syrup which
  3. customafforded a solid upon trituration with water
  4. customThe solid was collected
  5. washwashed with water
  6. customdried under vacuum at 40°

Sources & evidence

ORD record
ord-4246128159f345eeaa5ff449b4b6636e
Source dataset
uspto-grants-1985_08
Patent number
US04533739

Reaction notes

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