Methylhydrazine → HCID 178486239, compound

HRID 904809Notes

Reaction equation

HRID 904809 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:9]([OH:10])=[C:8]([C:11]#[N:12])[O:7][C:6]=2[CH:13]=1.[CH3:14][NH:15][NH2:16]>C1C=CC=CC=1>[CH3:14][NH:15][NH:16][C:11]([C:8]1[O:7][C:6]2[CH:13]=[CH:2][CH:3]=[CH:4][C:5]=2[C:9]=1[OH:10])=[NH:12]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 132821406-Chloro-3-hydroxy-1-benzofuran-2-carbonitrile

Product 1

HCID 178486239HCID 178486239, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Hydroxybenzo[b]furo-2-carbonitrile (1.40 g, 8.8 mmol, described in Example 3) was dissolved with heating in benzene (50 mL) and methyl hydrazine (1 mL, ca. 19 mmol) was added. The solution was stirred and refluxed for 2 hr and evaporated to dryness. The pasty residue (ca. 2 g) was applied in chloroform solution to chromatography on neutral alumina. Elution with 2% MeOH in CHCl3 (v/v) gave 3-hydroxybenzo[b]furan-2-carboximidic acid, 2-methylhydrazide (0.79 g): IR (CHCl3) 3510, 3480, 3450, 3200, 1635 and 1595 cm-1 ; and NMR (CDCl3) δ2.65 (3H, s), 5.7 (3H, broad), ca. 7.4 (1H, br), 7.2 (3H, m) and 7.75 (1H, d).

Workup

  1. temperaturerefluxed for 2 hr
  2. customevaporated to dryness
  3. washElution with 2% MeOH in CHCl3 (v/v)

Sources & evidence

ORD record
ord-4db77d66eaae46cf9ba7e2533756134c
Source dataset
uspto-grants-1983_12
Patent number
US04420476

Reaction notes

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