2-(3'-Methoxy-3-nitro-biphenyl-4-yl)-malonic acid dimethyl ester → 3'-Methoxy-3-nitrobiphenyl-4-acetic acid

HRID 11537Notes

Reaction equation

C[O:2][C:3](=[O:26])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[CH:11][C:10]=1[N+:23]([O-:25])=[O:24])C(OC)=O>Cl>[CH3:22][O:21][C:17]1[CH:16]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([CH2:4][C:3]([OH:26])=[O:2])=[C:10]([N+:23]([O-:25])=[O:24])[CH:11]=2)[CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 110 °C

Procedure

2-(3′-Methoxy-3-nitro-biphenyl-4-yl)-malonic acid dimethyl ester (4.4023 gms.) is suspended in 45 mL of 6N HCl and heated at 110° C. for 4 days. The reaction mixture is cooled to room temperature and the precipitate is collected by filtration. As the solid material is in rather large chunks, the solid purification is simplified by first dissolving the solid chunks in an excess of hot methanol, and subsequently concentrating the solution in vacuo to get a more manageable powder. This powder is then triturated with approximately 10 mL of methanol and filtered yielding (3′-methoxy-3-nitro-biphenyl-4-yl)-acetic acid in the amount of 2.0120 gms.

Workup

temperatureThe reaction mixture is cooled to room temperature
filtrationthe precipitate is collected by filtration
customthe solid purification
dissolutionby first dissolving the solid chunks in an excess of hot methanol
concentrationsubsequently concentrating the solution in vacuo
customto get a more manageable powder
customThis powder is then triturated with approximately 10 mL of methanol
filtrationfiltered

Sources & evidence

ORD record: ord-3093fa988b704db1b269470ed64cbdd4
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098236B2

Reaction notes

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