Water → HCID 10041267, compound

HRID 1828847Notes

Reaction equation

HRID 1828847 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([C:15]1[CH2:16][C:17]2[C:22]([C:23]=1[N:24]1CCCC1)=[CH:21][CH:20]=[CH:19][CH:18]=2)=O.Cl.[NH2:30]N.O>CCO>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[NH:30][N:24]=[C:23]2[C:22]3[C:17]([CH2:16][C:15]=12)=[CH:18][CH:19]=[CH:20][CH:21]=3

Participants

5

Reactant 3

HCID 962WaterHCID 115031Hydrazinium chlorideHCID 22058244HCID 22058244, compound

Product 1

HCID 10041267HCID 10041267, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

The compound from step b) was dissolved in EtOH (30 ml) and treated with hydrazine monohydrochloride (1.0 g, 13.3 mmol). The reaction vessel was fitted with an air-cooled condenser and heated to 80° C. for 36 h. The reaction mixture was cooled, water (10 ml) added, and the ethanol removed in vacuo. The residue was partitioned between EtOAc and water and the organic layer washed with water (2×). The organic layer was dried over MgSO4, evaporated, and the residue purified on alumina (Grade III), eluting with 0.5% EtOH/CH2Cl2 to obtain the title compound as a white solid (20.5 mg). 1H NMR (400 MHz, CDCl3) δ 7.72 (brs, 1H), 7.52 (d, J=7.6 Hz, 2H), 7.43–7.34 (m, 5H), 7.28 (t, J=9.6 Hz, 2H), 3.3 (brs, 2H), 2.56 (s, 3H), m/z (ES+) 314 (M+H)+.

Workup

  1. customThe reaction vessel was fitted with an air-cooled condenser
  2. temperatureThe reaction mixture was cooled
  3. customthe ethanol removed in vacuo
  4. customThe residue was partitioned between EtOAc and water
  5. washthe organic layer washed with water (2×)
  6. dry with materialThe organic layer was dried over MgSO4
  7. customevaporated
  8. customthe residue purified on alumina (Grade III)
  9. washeluting with 0.5% EtOH/CH2Cl2

Sources & evidence

ORD record
ord-4be811cfacad41fcbb808934b5f5a2fc
Source dataset
uspto-grants-2006_06
Patent number
US07060710B2

Reaction notes

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