Pyridine → 2-(p-Methoxybenzyloxy)acetic acid hydrazide

HRID 2251978Notes

Reaction equation

HRID 2251978 reaction equation
O.[NH2:2][NH2:3].N1C=CC=CC=1.C[O:11][C:12](=O)[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1>C(O)C>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][O:14][CH2:13][C:12]([NH:2][NH2:3])=[O:11])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24654Hydrazine hydrate (1:1)HCID 11790474(4-Methoxybenzyloxy)acetic acid methyl ester

Product 1

HCID 204730792-(p-Methoxybenzyloxy)acetic acid hydrazideYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add hydrazine hydrate (2.1 mL, 42.1 mmol) and pyridine (0.3 mL, 3.8 mmol) to a solution of (4-methoxy-benzyloxy)-acetic acid methyl ester (8.05 g, 38.3 mmol) in ethanol (100 mL, absolute). Heat the reaction to reflux under N2 overnight. Concentrate; add toluene and concentrate (2 times). Purify the residue by flash chromatography on silica gel eluting with 0-40% ACN/CH2Cl2 to afford the title compound (6.42 g, 80%) as clear oil. 1H NMR (400 MHz, DMSO) δ 3.73 (s, 3H); 3.84 (s, 2H); 4.24 (bs, 2H); 4.42 (s, 2H); 6.89 (d, 2H, J=8.3 Hz); 7.27 (d, 2H, J=8.3 Hz); 9.00 (bs, 1H). MS(IS) 209 (M−).

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureto reflux under N2 overnight
  4. concentrationConcentrate
  5. concentrationadd toluene and concentrate (2 times)
  6. customPurify the residue by flash chromatography on silica gel eluting with 0-40% ACN/CH2Cl2

Sources & evidence

ORD record
ord-35490aa243c746b1abeab1fbdb26c729
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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