Hydrazine → 4-amino-1-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butan-2-ol

HRID 474283Notes

Reaction equation

HRID 474283 reaction equation
[OH:1][CH:2]([CH2:16][O:17][C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=1[N:27]1[CH:31]=[N:30][C:29]([CH3:32])=[N:28]1)[CH2:3][CH2:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.NN>CCO>[NH2:5][CH2:4][CH2:3][CH:2]([OH:1])[CH2:16][O:17][C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=1[N:27]1[CH:31]=[N:30][C:29]([CH3:32])=[N:28]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 666684982-(3-hydroxy-4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)isoindoline-1,3-dione

Product 1

HCID 666657454-amino-1-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butan-2-olYield 81.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 2-(3-hydroxy-4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)isoindoline-1,3-dione (2.458 g, 5.62 mmol) in EtOH (28.1 mL) was added hydrazine (8.82 mL, 281 mmol). The mixture was heated at 50° C. for 1.5 h. The reaction mixture was cooled to rt and filtered. The filtrate was concentrated and taken up in CH2Cl2. Again, the solid was filtered off, and the filtrate was concentrated and purified by Prep-HPLC to obtain 4-amino-1-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butan-2-ol (1.4 g, 81% yield). LC-MS (M+H)+=308.2 1H NMR (500 MHz, methanol-d4) δ 9.25 (s, 1H), 8.12 (d, J=2.1 Hz, 1H), 8.10-7.98 (m, 2H), 4.39-4.26 (m, 2H), 4.26-4.15 (m, 1H), 3.25-3.08 (m, 2H), 2.48 (s, 3H), 2.05-1.86 (m, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. filtrationAgain, the solid was filtered off
  5. concentrationthe filtrate was concentrated
  6. custompurified by Prep-HPLC

Sources & evidence

ORD record
ord-29edc8d8e915417f8bebfbf570135d6c
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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