Benzene → HCID 178479873, compound

HRID 1241696Notes

Reaction equation

HRID 1241696 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:14]3[C:15](=[C:17]4[C:22](=[N:23][C:13]=3[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]2[CH3:24])[CH:21]=[CH:20][CH:19]=[CH:18]4)[CH:16]=1.C1C=CC=CC=1.CO.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[OH:2][C:3]1[CH:4]=[C:5]2[C:14]3[C:15](=[C:17]4[C:22](=[N:23][C:13]=3[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]2[CH3:24])[CH:21]=[CH:20][CH:19]=[CH:18]4)[CH:16]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 887MethanolHCID 516892Sodium BicarbonateHCID 11130764HCID 11130764, compound2×

Product 1

HCID 178479873HCID 178479873, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The general procedure (Method K, described below) applied to 6-methoxy-8-methyl-8H-quino[4,3,2-kl]acridine, 31 (400 mg, 1.28 mmol), dry benzene (100 ml) aluminium chloride (900 mg), methanol (100 ml), sat. aq. sodium hydrogen carbonate (40 ml), and ethyl acetate (100 ml) gave the title compound (381 mg, 1.27 mmol, 99.7%).

Sources & evidence

ORD record
ord-6adbecf0e8db4751a0fa80b699677c7c
Source dataset
uspto-grants-2006_10
Patent number
US07115619B2

Reaction notes

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