Pyridine → HCID 21561983, compound

HRID 1580532Notes

Reaction equation

HRID 1580532 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C:12]([NH2:14])=[CH:11][CH:10]=[CH:9]2)=[N+:2]=[N-:3].N1C=CC=CC=1.[C:21](Cl)(=[O:23])[CH3:22]>CCOCC>[C:21]([NH:14][C:12]1[C:13]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[N:1]=[N+:2]=[N-:3])[CH:9]=[CH:10][CH:11]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 120253881-Naphthalenamine, 8-azido-

Product 1

HCID 21561983HCID 21561983, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 8-azido-1-naphthylamine (1.84 g., 0.01 mole) in 70 ml. of pyridine was added a solution of acetyl chloride (0.784 g., 0.01 mole) in 10 ml. of ether. The mixture was warmed on a steam bath for 30 minutes. The solvents were removed in vacuo and the residue washed with water and dried. Recrystallization from hexane provided 1-acetamido-8-azidonaphthalene in the form of colorless, long needles having a yield of 2.1 g., 93 percent, m.p. 148°C.-149°C., Lit. m.p. 147°C.-148°C. and an analysis of: Calcd. for C12H10N4C: C, 63.70; H, 4.46; N, 24.77 Found: C, 63.90; H, 4.14; N, 24.66

Workup

  1. temperatureThe mixture was warmed on a steam bath for 30 minutes
  2. customThe solvents were removed in vacuo
  3. washthe residue washed with water
  4. customdried
  5. customRecrystallization from hexane

Sources & evidence

ORD record
ord-c5767b7fb6884a89b64abee958a101b7
Source dataset
uspto-grants-1976_01
Patent number
US03933497

Reaction notes

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