Sodium Hydroxide → HCID 13282156, compound

HRID 904806Notes

Reaction equation

HRID 904806 reaction equation
[CH3:1][N:2]([C:4]([C:6]1[O:10][C:9]2[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:8]=2[C:7]=1O)=[NH:5])[NH2:3].[OH-].[Na+]>>[Cl:15][C:12]1[CH:13]=[CH:14][C:8]2[C:7]3[C:6]([O:10][C:9]=2[CH:11]=1)=[C:4]([NH2:5])[N:2]([CH3:1])[N:3]=3

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 136128186HCID 136128186, compound

Product 1

HCID 13282156HCID 13282156, compound

Procedure

The crude 6-chloro-3-hydroxybenzo[b]furan-2-carboximidic acid, 1-methylhydrazide, (25 g, described in Example 5) was combined with polyphosphoric acid (250 g) and the mixture was stirred at 70°-80° C. for 4 hr. The hot mixture was poured into ice-water and the solution was made alkaline with 50% aqueous sodium hydroxide. The product was extracted several times with methylene chloride and the combined extracts were dried and evaporated. The crude product was triturated with diethyl ether to give the title compound (13 g): mp 210°-211° C.; IR (mineral oil) 3370, 3240 and 3120 cm-1 ; UV max (MeOH) 227 nm (ε=15400), 253 (22100), shoulder 209 nm; NMR (DMSO-d6) δ3.7 (3H, s), 5.4 (2H, s), and 7.5 (3H, m); and Anal. Calcd for C10H8ClN3O: C, 54.19% H, 3.64%, N, 18.96% and Found: C, 53.91% H, 3.60% N, 18.90%.

Workup

  1. extractionThe product was extracted several times with methylene chloride
  2. customthe combined extracts were dried
  3. customevaporated
  4. customThe crude product was triturated with diethyl ether

Sources & evidence

ORD record
ord-ec4733203be546ac8b18d980521980d7
Source dataset
uspto-grants-1983_12
Patent number
US04420476

Reaction notes

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