Hydrazine → HCID 16637125, compound

HRID 1406641Notes

Reaction equation

HRID 1406641 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14](OCC)=[O:15])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[NH2:21][NH2:22]>C(O)C>[CH3:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([NH:21][NH2:22])=[O:15])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 6465433HCID 6465433, compound

Product 1

HCID 16637125HCID 16637125, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 6{13} (7.66 g, 27.7 mmol, 1 equiv.), anhydrous hydrazine (2.6 mL, 83.2 mmol, 3 equiv.), ethanol (55.4 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{13} (6.10 g, 84%) as a beige solid. 1H-NMR (500 MHz, CDCl3): δ 8.14 (br s, 1H), 7.18 (d, 2H, J=8.0 Hz), 7.12 (d, 2H, J=8.0 Hz), 3.84 (br s, 2H), 3.46 (s, 2H), 3.06 (s, 2H), 2.52 (br s, 4H), 2.45 (br s, 4H), 2.33 (s, 3H). 13C-NMR (125 MHz, CDCl3): δ 170.5, 136.7, 134.6, 129.1, 128.9, 62.5, 60.5, 53.6, 52.9, 21.1.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{13} (6.10 g, 84%) as a beige solid

Sources & evidence

ORD record
ord-6ab93a58c879421fbdd3ac8017a89351
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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