Hydrochloric Acid → 2-(3-hydroxy-4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)isoindoline-1,3-dione
Reaction equation
[OH:1][CH:2]([CH2:17][O:18][C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[N:28]1[CH:32]=[N:31][C:30]([CH3:33])=[N:29]1)[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O)=[O:7].Cl.O1CCOCC1>>[OH:1][CH:2]([CH2:17][O:18][C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[N:28]1[CH:32]=[N:31][C:30]([CH3:33])=[N:29]1)[CH2:3][CH2:4][N:5]1[C:6](=[O:7])[C:8]2[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10]1=[O:12]Participants
4
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 2-(3-hydroxy-4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butylcarbamoyl)benzoic acid (2.56 g, 5.62 mmol) and hydrogen chloride in dioxane (42.2 mL, 169 mmol) was heated at 100° C. for 45 min. The reaction was cooled to rt, and then extracted with EtOAc. The combined organic layers were concentrated to get 2-(3-hydroxy-4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)isoindoline-1,3-dione which was used as-is in the next step. LC-MS (M+H)+=438.2. 1H NMR (500 MHz, methanol-d4) δ 9.26 (s, 1H), 8.13-7.97 (m, 3H), 7.87-7.83 (m, 2H), 7.83-7.77 (m, 2H), 4.36 (dd, J=9.9, 3.5 Hz, 1H), 4.27 (dd, J=9.8, 6.1 Hz, 1H), 4.12 (dt, J=6.0, 2.9 Hz, 1H), 3.95-3.81 (m, 2H), 2.48 (s, 3H), 2.08-1.87 (m, 2H).
Workup
- temperatureThe reaction was cooled to rt
- extractionextracted with EtOAc
- concentrationThe combined organic layers were concentrated
Sources & evidence
- ORD record
- ord-e8fc85a0f2084aaaa89db672ec1f3dcd
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637523B2
Reaction notes
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