Acetyl chloride → 4-Methoxy-benzo[a]phenazine-11-carboxylic Acid Methyl Ester

HRID 719184Notes

Reaction equation

HRID 719184 reaction equation
[C:1](Cl)(=O)C.[CH3:5][O:6][C:7]1[C:12]2=[CH:13][CH:14]=[C:15]3[C:24]([N:23]=[C:22]4[C:17]([CH:18]=[CH:19][CH:20]=[C:21]4[C:25]([OH:27])=[O:26])=[N:16]3)=[C:11]2[CH:10]=[CH:9][CH:8]=1>CO>[CH3:1][O:26][C:25]([C:21]1[C:22]2[C:17](=[N:16][C:15]3[C:24]([N:23]=2)=[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([O:6][CH3:5])[C:12]2=[CH:13][CH:14]=3)[CH:18]=[CH:19][CH:20]=1)=[O:27]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 111202464-Methoxy-benzo[a]phenazine-11-carboxylic Acid

Product 1

HCID 695968574-Methoxy-benzo[a]phenazine-11-carboxylic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (4.6 mL) was added dropwise to a suspension of 4-methoxy-benzo[a]phenazine-11-carboxylic acid (II.1, see Reference Example 1A, 4.9 g) in methanol (50 mL). The mixture was heated to reflux for 4 hours. The volatiles were then removed in vacuo to yield the title compound as a dark solid (quantitative yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customThe volatiles were then removed in vacuo

Sources & evidence

ORD record
ord-145bfd4fba4d4104beae24ce0650b988
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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