Lithium Hydroxide → 2'-Methyl-2-nitro-[1,1'-biphenyl]-4-carboxylic acid

HRID 219777Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19].[OH-].[Li+]>C1COCC1.O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 2′-methyl-2-nitro-1,1′-biphenyl-4-carboxylate, prepared in step 1 (2.5 g, 9.2 mmol) was dissolved in dry THF (20 mL) and cooled to 0° C. To this solution was added lithium hydroxide (1.15 g, 27.6 mmol) in water (5 mL) and the mixture was stirred at RT for 4 h. The solvents were concentrated and the aqueous residue was washed with EtOAc. The aqueous layer was separated and acidified with 1.5N HCl to pH 2-3 and extracted with DCM. DCM was washed with water and dried over sodium sulphate and evaporated under reduced pressure to obtain the title compound as a yellow solid (1.6 g, 70%). 1H NMR: (DMSO-d6, 400 MHz) δ 13.67 (bs, 1H), 8.49 (s, 1H), 8.26-8.24 (d, 1H), 7.58-7.56 (m, 1H), 7.35-7.32 (m, 2H), 7.27-7.12 (d, 1H), 7.10 (d, 1H), 2.09-1.99 (s, 3H). LC/MS (Method A): 255.9 (M−H)−. HPLC (Method B) Rt 1.79 min (Purity: 99.16%).

Workup

concentrationThe solvents were concentrated
washthe aqueous residue was washed with EtOAc
customThe aqueous layer was separated
extractionextracted with DCM
washDCM was washed with water
dry with materialdried over sodium sulphate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-38cbc011b8724d5397bc3d2590a7ad68
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202865B2

Reaction notes

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