Pyridine → HCID 178445143, compound

HRID 2198547Notes

Reaction equation

HRID 2198547 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9][C:10]([N:12]([CH3:25])[C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[C:15](=[O:24])[N:16]([CH3:23])[C:17]3=[O:22])=[O:11])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:32](Cl)(=[O:38])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C(#N)C>[C:32]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9][C:10]([N:12]([CH3:25])[C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[C:15](=[O:24])[N:16]([CH3:23])[C:17]3=[O:22])=[O:11])=[CH:4][CH:3]=1)(=[O:38])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67340Hexanoyl chlorideHCID 178481327HCID 178481327, compound

Product 1

HCID 178445143HCID 178445143, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

1-p-Aminophenyl-4-methyl-4-(2-methyl-1,3-dioxoisoindolin-4-yl)semicarbazide (1.5 g, 4.5 mmole) and pyridine (1 ml) were dissolved in 30 ml of acetonitrile under nitrogen and cooled to +5° C. in an ice bath. Hexanoyl chloride (0.6 g, 4.5 mmole) in 5 ml of acetonitrile was added dropwise. The mixture was stirred 11/2 hours at ice-bath temperature. The resulting solid was filtered to give 0.6 g of product, m.p. 115°-118° C. Recrystallization from acetonitrile and ethyl acetate gave 0.32 g (16% yield) of product, m.p. 147°-149° C.

Workup

  1. temperaturecooled to +5° C. in an ice bath
  2. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-8fae3885a0de4347ade7d9a777d647ed
Source dataset
uspto-grants-1982_11
Patent number
US04358525

Reaction notes

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