Ethanol → HCID 59341168, compound

HRID 449022Notes

Reaction equation

HRID 449022 reaction equation
[Cl:1][C:2]1[C:3]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)[N:9]2C(=O)C3C(=CC=CC=3)C2=O)=[N:4][CH:5]=[CH:6][N:7]=1.NN.CCO>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH:8]([NH2:9])[C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:24][CH:25]=2)=[N:4][CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 866360272-[(3-Chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-isoindole-1,3-dione

Product 1

HCID 59341168HCID 59341168, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[(3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-isoindole-1,3-dione (1.04 g, 0.0023 mol) and anhydrous hydrazine (0.247 mL, 0.0078 mol) in DCM (8.8 mL)/EtOH (6 mL) was stirred at rt overnight. The white precipitate (phthalic hydrazide) was filtered and washed with DCM. The filtrate was collected and concentrated in vacuo and purified by flash column chromatography using 10%-30% EtOAc in hexanes to afford 570 mg of the title compound as an orange oily solid. 1H NMR (400 MHz, CDCl3): δ 2.38 (br. s., 2H), 5.54 (s, 1H), 6.89-7.01 (m, 4H), 7.09 (t, J=7.45 Hz, 1H), 7.27-7.36 (m, 4H), 8.26 (d, J=2.27 Hz, 1H), 8.53 (d, J=2.53 Hz, 1H). MS (ES+): m/z 294.72 (90) [MH+]. HPLC: tR=2.15 min (Open Lynx, polar—5 min).

Workup

  1. filtrationThe white precipitate (phthalic hydrazide) was filtered
  2. washwashed with DCM
  3. customThe filtrate was collected
  4. concentrationconcentrated in vacuo
  5. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-c9b046460d184ea3acfb6d4aaf3d00cb
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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