Tetrachlorophthalic anhydride → HCID 86703352, compound

HRID 2173679Notes

Reaction equation

HRID 2173679 reaction equation
[OH:1][C:2]1[C:11]2[CH2:12][CH2:13][CH2:14][CH2:15][N:9]3[C:10]=2[C:5]([C:6](=O)[CH2:7][CH2:8]3)=[CH:4][CH:3]=1.[Cl:17][C:18]1[C:19]([Cl:31])=[C:20]([Cl:30])[C:21]([Cl:29])=[C:22]2[C:27](=[O:28])[O:26][C:24](=[O:25])[C:23]=12>C1C(Cl)=CC=C(Cl)C=1>[Cl:17][C:18]1[C:19]([Cl:31])=[C:20]([Cl:30])[C:21]([Cl:29])=[C:22]([C:27]([C:3]2[CH:4]=[C:5]3[C:10]4=[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][N:9]4[CH2:8][CH2:7][CH2:6]3)[C:2]=2[OH:1])=[O:28])[C:23]=1[C:24]([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 8326Tetrachlorophthalic anhydrideHCID 86703353HCID 86703353, compound

Product 1

HCID 86703352HCID 86703352, compound

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Procedure

To a solution of 9-hydroxy-2,3,5,6,7,8-hexahydro-1H-azepino[3,2,1-ij]quinolone (30 mg) in dichlorobenzene (1 mL), tetrachlorophthalic anhydride (0.13 mL) was added. After stirring at reflux for 2 hours, the solvent was removed, and the resulting crude product purified by preparative HPLC (gradient of ACN in 0.1% TFA in H2O) to provide the title compound (20 mg) as a green solid: MS expected 490 (C21H18Cl4NO4+, M+), found 490.

Workup

  1. temperatureat reflux for 2 hours
  2. customthe solvent was removed
  3. customthe resulting crude product purified by preparative HPLC (gradient of ACN in 0.1% TFA in H2O)

Sources & evidence

ORD record
ord-5fa2e79650c34c8da527b8ff16bc5e6f
Source dataset
uspto-grants-2015_06
Patent number
US09056885B2

Reaction notes

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