Hydrazine hydrate (1:1) → HCID 18763439, compound

HRID 431386Notes

Reaction equation

HRID 431386 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=1)[C:16](OC)=[O:17].O.[NH2:27][NH2:28]>CO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=1)[C:16]([NH:27][NH2:28])=[O:17]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18763429Methyl 3-[(2-naphthyl)methoxy]-5-nitrobenzoate

Product 1

HCID 18763439HCID 18763439, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3-[(2-naphthyl)methoxy]-5-nitrobenzoate (0.97 g, 2.87 mmol) and hydrazine hydrate (0.56 mL, 11.5 mmol) in MeOH (50 mL) was stirred under reflux overnight. Formation of solid hydrazide from a boiling mixture was observed in the morning. Mixture was cooled, solid filtered and air-dried. Greenish-white plates, yield 0.60 g (62%). 1H NMR (DMSO-d6, 400 MHz), δ: 10.15 (br.s, 1H); 8.27 (s, 1H); 8.05-7.91 (m, 6H); 7.63 (d, J=7.5 Hz, 1H); 7.59-7.52 (m, 2H); 5.48 (s, 2H); 4.66 (br.s, 2H).

Workup

  1. temperatureunder reflux overnight
  2. temperatureMixture was cooled
  3. filtrationsolid filtered
  4. customair-dried

Sources & evidence

ORD record
ord-cc61340122ba4397a062804991bbfd65
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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