Hydrochloric Acid → HCID 19433631, compound

HRID 1737077Notes

Reaction equation

C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH:15][C:16](=[O:34])[C:17]([NH:19][C:20]1[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([C:29]([O:31]CC)=[O:30])=[CH:23]3)=[O:18])=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+].Cl>N1C=CC=CC=1>[O:34]=[C:16]([NH:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]2)[C:17]([NH:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([C:29]([OH:31])=[O:30])=[CH:23]2)=[O:18]

Participants

Conditions

Temperature: 60 °C

Procedure

5,5'-[(1,2-dioxo-1,2-ethanediyl)diimino]bis-1H-indole-2-carboxylic acid diethyl ester (220 mg, 0.48 mM) is suspended in pyridine (9 mL) and treated with 1N NaOH (1.5 mL). The milky mixture is heated to 60° C. under nitrogen. After 24 hrs N NaOH again added (1 mL) and the reaction heated another 3 hrs. The reaction is then neutralized by the addition of 1N HCl (2.5 mL) and concentrated to one-half volume at less than 20 torr. The residue is then treated with 1N HCl (50 mL) and centrifuged giving a residual slightly pink solid. This is is washed with water, centrifuged, and dried in the vacuum oven leaving the product 5,5'-[(1,2-dioxo-1,2-ethanediyl)diimino]bis-1H-indole-2-carboxylic acid (148 mg).

Workup

temperaturethe reaction heated another 3 hrs
concentrationconcentrated to one-half volume at less than 20 torr
additionThe residue is then treated with 1N HCl (50 mL)
customcentrifuged giving a residual slightly pink solid
washThis is is washed with water
customcentrifuged, and dried in the vacuum oven

Sources & evidence

ORD record: ord-45a160d816e146e6868d641e557af927
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05541339

Reaction notes

Loading…