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Acetic Anhydride → 7-[(acetoxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-ethyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-one

HRID 847518
Notes
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Reaction equation

HRID 847518 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]2[C:19](=[O:50])[CH:20]([CH:23]([OH:49])[C:24]3[N:25]=[CH:26][N:27]([C:30]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:28]=3[CH3:29])[CH2:21][CH2:22][C:11]=12)[CH3:9]>N1C=CC=CC=1>[C:1]([O:49][CH:23]([C:24]1[N:25]=[CH:26][N:27]([C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:28]=1[CH3:29])[CH:20]1[C:19](=[O:50])[N:12]2[C:13]3[C:18]([C:10]([CH2:8][CH3:9])=[C:11]2[CH2:22][CH2:21]1)=[CH:17][CH:16]=[CH:15][CH:14]=3)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1005366010-ethyl-8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one

Product 1

HCID 101002317-[(acetoxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-ethyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (2.0 ml) was added to a solution of 10-ethyl-8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (2.15 g) in pyridine (10 ml). After being stirred at room temperature for 20 hours, the solution was evaporated in vacuo. The residue was dissolved in toluene (30 ml) and the solution was evaporated in vacuo to remove pyridine and acetic anhydride. This operation was repeated further three times to give 7-[(acetoxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-ethyl-8,9-dihydropyrido-[1,2-a]indol-6(7H)-one as an amorphous powder. This crude product was used in the next reaction without further purification.

Workup

  1. customthe solution was evaporated in vacuo
  2. dissolutionThe residue was dissolved in toluene (30 ml)
  3. customthe solution was evaporated in vacuo
  4. customto remove pyridine and acetic anhydride

Sources & evidence

ORD record
ord-af1cb39fdd5842b89381c211df01dcb0
Source dataset
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05141945

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes