Acetic Anhydride → HCID 19607992, compound

HRID 745059Notes

Reaction equation

HRID 745059 reaction equation
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:12](=[O:30])[C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:29])[C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)=[CH:15][CH:14]=2)[CH2:3]1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>ClCCl>[C:31]([NH:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:12](=[O:30])[C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:29])[C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)=[CH:17][CH:18]=2)[CH2:3]1)(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19607782HCID 19607782, compound

Product 1

HCID 19607992HCID 19607992, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-amino-1-[4-(3,5-dichlorobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (0.44 g) are added dichloromethane (5 ml) and acetic anhydride (0.12 g) and the mixture is stirred for 1 hour. The reaction mixture is concentrated and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane→dichloromethane:methanol=50:1) to give 3-acetylamino-1-[4-(3,5-dichlorobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (0.3 g) as colorless amorphous.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane→dichloromethane:methanol=50:1)

Sources & evidence

ORD record
ord-6997fc7cf2784f3f9e0b6b8af1eb8cd9
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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