Ethanol → 2-(3',4'-dimethylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazole-7-carboxylic Acid Hydrochloride

HRID 25317Notes

Reaction equation

HRID 25317 reaction equation
C[C:2]1([CH:15]=O)[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1.[ClH:17].Cl.[NH2:19][C:20]1[C:29]([NH2:30])=[C:28]2[C:23]([CH:24]=[C:25]([C:32]([OH:34])=[O:33])[CH:26]=[C:27]2[OH:31])=[CH:22][CH:21]=1.S(=O)(O)[O-].[Na+].[CH3:40]CO>O>[ClH:17].[CH3:15][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([C:40]3[NH:19][C:20]4[CH:21]=[CH:22][C:23]5[C:28](=[C:27]([OH:31])[CH:26]=[C:25]([C:32]([OH:34])=[O:33])[CH:24]=5)[C:29]=4[N:30]=3)[CH:14]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 702EthanolHCID 22566617HCID 22566617, compoundHCID 23665763Sodium BisulfiteHCID 695479317,8-Diamino-1-hydroxy-3-naphthoic acid dihydrochloride

Product 1

HCID 695489792-(3',4'-dimethylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazole-7-carboxylic Acid HydrochlorideYield 33%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To an agitated solution of 3,4-dimethylbiphenyl-3-carbaldehyde (0.019 g, 0.09 mmol) in EtOH (0.80 mL) was added 7,8-Diamino-1-hydroxy-3-naphthoic acid dihydrochloride (0.024 g, 0.08 mmol) and sodium bisulfite (0.02 g) in water (0.20 mL). The solution was heated to 60° C. and agitated overnight. The solution was cooled to room temperature and concentrated under reduced pressure. The tan residue was subjected to HPLC (ODS-A, gradient 10-90% CH3CN/water 0.1% TFA) to provide the title compound (0.015 g, 33%) MS(ES) m/z 409 [M+H].

Workup

  1. temperatureThe solution was cooled to room temperature
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-deddf14e1e8344839a5e34dde35656cd
Source dataset
uspto-grants-2005_02
Patent number
US06858630B2

Reaction notes

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