Hydrochloric Acid → Pyrroloquinoline Quinone

HRID 517624

Reaction equation

C(=O)([O-])[O-].[K+].[K+].C[O:8][C:9]([C:11]1[NH:33][C:14]2[C:15]3[C:16]([C:29]([O:31]C)=[O:30])=[CH:17][C:18]([C:25]([O:27]C)=[O:26])=[N:19][C:20]=3[C:21](=[O:24])[C:22](=[O:23])[C:13]=2[CH:12]=1)=[O:10].Cl>O>[O:23]=[C:22]1[C:21](=[O:24])[C:20]2[N:19]=[C:18]([C:25]([OH:27])=[O:26])[CH:17]=[C:16]([C:29]([OH:31])=[O:30])[C:15]=2[C:14]2[NH:33][C:11]([C:9]([OH:10])=[O:8])=[CH:12][C:13]1=2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of potassium carbonate (about 439 g, 3.18 mol) in water (about 4.5 L), 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester (about 200 g, 0.53 mol) is added at about 25° C. The reaction mixture is allowed to stir at about 80° C. over a period of about 12 hours. Completion of reaction is monitored by HPLC. Thereafter, the reaction mixture is acidified (pH: 2.0) with 1N hydrochloric acid to precipitate the product [4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid] as dark red solid (about 160 g, 91%). 1H NMR (DMSO-d6, 300 MHz): 7.21 (s, 1H), 8.60 (s, 1H), 13.42 (s, 1H); LC-MS (ESI): 329 (M-H), Purity by HPLC: 98%.

Workup

customCompletion of reaction
customto precipitate the product [4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid] as dark red solid (about 160 g, 91%)

Sources & evidence

ORD record: ord-e6057860efef4aeabb53cc17c6cff7bc
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115128B2

Linked notes

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