Water → HCID 2046430, compound

HRID 1631867Notes

Reaction equation

HRID 1631867 reaction equation
C[O:2][C:3](=O)[CH2:4][NH:5][C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[O:7].O.[NH2:20][NH2:21].O>CCO>[NH:20]([C:3](=[O:2])[CH2:4][NH:5][C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[O:7])[NH2:21]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 19789843HCID 19789843, compound

Product 1

HCID 2046430HCID 2046430, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above compound 2a (3.3 g, 13.1 mmol) was heated at 60° C. with hydrazine hydrate (3.5 mL, 65 mmol) in EtOH (30 mL) for 2 hours. After cooling at room temperature, water (10 mL) was added. The resulting white precipitate was filtered and dried under vacuum to give hydrazide derivative 3a (2.6 g, 79%). 1H NMR (acetone-d6) δ 3.91 (d, J=5.9 Hz, 2H, CH2), 7.55-7.58 (m, 3H, Ar), 7.68 (dd, J=1.1 and 7.0 Hz, 1H, Ar), 7.98 (d, J=8.0 Hz, 1H, Ar), 8.02 (d, J=8.3 Hz, 2H, Ar), 8.35 (m, 1H, NH), 8.74 (t, J=6.3 Hz, 1H, NH), 9.31 (bs, 1H, NH); 13C NMR (acetone-d6) δ 41.08 (CH2), 124.88, 124.92, 125.13, 125.72, 126.12, 126.56, 128.07, 129.67, 129.80, 129.83, 133.08, 134.46, 168.34 (CO), 168.91 (CO).

Workup

  1. filtrationThe resulting white precipitate was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-1e859b2595cf4b0c9e1e386e50155988
Source dataset
uspto-grants-2014_07
Patent number
US08791299B2

Reaction notes

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