Hydrazine → HCID 86681342, compound

HRID 1406632Notes

Reaction equation

HRID 1406632 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13](OCC)=[O:14])[CH2:8][CH2:7]1.[NH2:21][NH2:22]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]([NH:21][NH2:22])=[O:14])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 6464821HCID 6464821, compound

Product 1

HCID 86681342HCID 86681342, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 6{8} (6.78 g, 22.8 mmol, 1 equiv.), anhydrous hydrazine (2.9 mL, 91.4 mmol, 4 equiv.), ethanol (31.4 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{8} (5.04 g, 78%) as a light yellow oil. 1H-NMR (500 MHz, CDCl3): δ 8.15 (br s, 1H), 7.27 (br s, 1H) 7.21-7.12 (m, 3H), 3.82 (br s, 2H) 3.42 (s, 2H), 3.03 (s, 2H), 2.49 (br s, 4H), 2.41 (br s, 4H). 13C-NMR (125 MHz, CDCl3): δ 170.3, 140.0, 134.0, 129.3, 128.8, 127.1, 126.9, 62.0, 60.4, 53.4, 52.8.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{8} (5.04 g, 78%) as a light yellow oil

Sources & evidence

ORD record
ord-e1481ea3bc0447fd80f4b60b404f265a
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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