5-(3,4-Dimethylphenyl)furan-2-carbaldehyde → HCID 22566656, compound

HRID 25325Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][C:12]([CH:14]=O)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].Cl.Cl.[NH2:18][C:19]1[C:28]([NH2:29])=[C:27]2[C:22]([CH:23]=[C:24]([C:31]([OH:33])=[O:32])[CH:25]=[C:26]2[OH:30])=[CH:21][CH:20]=1.S(=O)(O)[O-].[Na+]>CCO.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][C:12]([C:14]3[NH:18][C:19]4[CH:20]=[CH:21][C:22]5[C:27](=[C:26]([OH:30])[CH:25]=[C:24]([C:31]([OH:33])=[O:32])[CH:23]=5)[C:28]=4[N:29]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

To an agitated solution of 5-(3,4-dimethylphenyl)-furan-2-carbaldehyde (0.030 g, 0.15 mmol) in EtOH (0.80 mL) was added 7,8-diamino-1-hydroxy-3-naphthoic acid dihydrochloride (0.029 g, 0.10 mmol) and sodium bisulfite (30 mg) in water (0.20 mL). The solution was heated to 60° C. and agitated overnight. The solution was cooled to room temperature, the tan precipitate was isolated by filtration and washed with water and ethyl acetate to provide the title compound (0.007 g, 15%) MS(ES) m/z 399 [M−H].

Workup

temperatureThe solution was cooled to room temperature
customthe tan precipitate was isolated by filtration
washwashed with water and ethyl acetate

Sources & evidence

ORD record: ord-779bf0a63f884c359b2c9f75273cc29b
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858630B2

Reaction notes

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