Sodium Hydroxide → HCID 71537191, compound

HRID 1519289Notes

Reaction equation

[OH-].[Na+].C[O:4][C:5]([C:7]1[C:8]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])=[CH:9][CH:10]=[C:11]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[N:17]=2)[CH:12]=1)=[O:6]>O.O1CCOCC1>[CH3:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([C:16]2[N:17]=[C:13]([C:11]3[CH:12]=[C:7]([C:5]([OH:6])=[O:4])[C:8]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[N+:32]([O-:34])=[O:33])=[CH:9][CH:10]=3)[S:14][CH:15]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium hydroxide (200 mg, 5 mmol) was added to a suspension of 4-[4-(4-methoxy-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid methyl ester (187 mg) in a mixture of water (8 mL) and dioxane (8 mL). The reaction mixture was stirred at 50° C. for 2 h. The reaction mixture was evaporated to dryness and water (15 mL) was added. The mixture was filtered and the filtrate was made acidic to pH 3-4 by the addition of concentrated HCl. The precipitate was collected by filtration and dried to give 4-[4-(4-methoxy-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (100 mg, 37% for two steps). 1H NMR (300 MHz, DMSO-d6) δ 13.17 (br s, 1H), 8.56 (d, J=1.8 Hz, 1H), 8.24 (dd, J=8.0, 1.9 Hz, 1H), 8.11-8.16 (m, 2H), 8.01 (d, J=8.8 Hz, 2H), 7.76-7.81 (m, 1H), 7.63-7.68 (m, 1H), 7.41-7.47 (m, 2H), 7.05 (d, J=8.8 Hz, 2H), 3.82 (s, 3H).

Workup

customThe reaction mixture was evaporated to dryness and water (15 mL)
additionwas added
filtrationThe mixture was filtered
additionthe filtrate was made acidic to pH 3-4 by the addition of concentrated HCl
filtrationThe precipitate was collected by filtration
customdried

Sources & evidence

ORD record: ord-a600094f560946ccb4623c34f08881d0
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073881B2

Reaction notes

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