4,7-Dichloroisatin → 4-(5,8-Dichloro-9H-1,2,3a,4,9,10-hexaaza-cyclopenta[b]fluoren-3-ylmethyl)-phenol

HRID 1822904Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]2[C:3]=1[C:4](=O)[C:5](=O)[NH:6]2.[NH2:14][N:15]1[C:19]([NH2:20])=[N:18][N:17]=[C:16]1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>C(O)C(F)(F)F.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]2[C:3]=1[C:4]1[C:5]([NH:6]2)=[N:20][C:19]2=[N:18][N:17]=[C:16]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[N:15]2[N:14]=1

Participants

Conditions

Temperature: 125 °C

Procedure

In a pressure tube, 0.60 mmol of 4,7-dichloro-1H-indole-2,3-dione (130 mg) and 0.65 mmol of 4-(4,5-diamino-4H-[1,2,4]triazol-3-ylmethyl)-phenol (133.5 mg) in a mixture of trifluoroethanol (8 mL) and water (4 mL) was stirred at 125° C. overnight (16 hr). The mixture was cooled to room temperature, allowed to crystallize for 2 hours. The precipitated product was collected by filtration, washed with MeOH+water 1:1, then with chilled MeOH. Dried on high vacuum.

Workup

temperatureThe mixture was cooled to room temperature
customto crystallize for 2 hours
filtrationThe precipitated product was collected by filtration
washwashed with MeOH+water 1:1
customDried on high vacuum

Sources & evidence

ORD record: ord-cdd109a185f343d2beb5c7ac7598ca4d
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037909B2

Reaction notes

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