Hydrochloric Acid → 2-[(Dimethylamino)methyl]-2'-methylbiphenyl-4-carboxylic acid

HRID 400747Notes

Reaction equation

[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[C:9]([C:11]([O:13]C)=[O:12])[CH:8]=[CH:7][C:6]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[CH3:3].Cl>O>[CH3:3][N:2]([CH2:4][C:5]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:6]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[CH3:1]

Participants

Conditions

Temperature: 105 °C

Procedure

To a solution of methyl 2-[(dimethylamino)methyl]-2′-methylbiphenyl-4-carboxylate obtained in step 4 (687 mg; 2.42 mmol) in water (20 mL) at RT was treated with HCl (12 mL; 5 M; 60 mmol). The reaction mixture was refluxed at 105° C. for 4 hours, evaporated under vacuum, taken up in ACN and evaporated under vacuum to give the title compound as a light yellow powder (719 mg; 96%). 1H NMR (DMSO-d6) δ 13.23 (br s, 1H), 10.31 (br s, 1H), 8.47 (s, 1H), 8.03 (d, J=7.2 Hz, 1H), 7.38-7.31 (m, 4H), 7.20 (d, J=7.2 Hz, 1H), 4.32 (d, J=13.2 Hz, 1H), 3.87 (d, J=13.2 Hz, 1H), 2.61 (s, 3H), 2.50 (s, 3H), 1.98 (s, 3H). HPLC (Method A) Rt 2.52 min (Purity 100.0%).

Workup

customevaporated under vacuum
customevaporated under vacuum

Sources & evidence

ORD record: ord-7450c5ba5cfc41f59954834eea8e4401
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741923B2

Reaction notes

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