Ammonia → HCID 15915858, compound

HRID 444230Notes

Reaction equation

HRID 444230 reaction equation
[NH3:1].[C:2]([NH:5][C:6]1[C:7](=[O:20])[C:8]2[C:13]([C:14](=[O:17])[C:15]=1Br)=[CH:12][C:11]([CH3:18])=[C:10]([CH3:19])[CH:9]=2)(=[O:4])[CH3:3]>[N+](C1C=CC=CC=1)([O-])=O>[C:2]([NH:5][C:6]1[C:7](=[O:20])[C:8]2[C:13]([C:14](=[O:17])[C:15]=1[NH2:1])=[CH:12][C:11]([CH3:18])=[C:10]([CH3:19])[CH:9]=2)(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 246349N-(3-Bromo-6,7-dimethyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)ethanimidic acid

Product 1

HCID 15915858HCID 15915858, compound

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
216 °C

Procedure

Dry ammonia was passed through a stirred refluxing solution of 2-acetamido-3-bromo-6,7-dimethyl-1,4-naphthoquinone (7.5 g) in nitrobenzene (50 ml) for 1 hr. and the mixture cooled. The red solid which separated was filtered off, washed well with ether-petrol and then water to give 4.46 g. (77%) of material of mp 212°-216° C. Recrystallisation from ethanol raised the melting point to 216° C., ν max(mull), 3400, 3270, 1675, 1665, 1630 cm-1. δ (DMSO) 2.05 (3H,s); 2.35 (6H,s); 6.64 (2H, exchangeable s); 7.71(2H,s); 9.00 (1H, exchangeable s.) (Found; C, 65.07; H, 5.43; N, 10.66; C14H14N2O3 requires; C, 65.10; H, 5.46; N, 10.85%).

Workup

  1. temperatureand the mixture cooled
  2. customThe red solid which separated
  3. filtrationwas filtered off
  4. washwashed well with ether-petrol
  5. customwater to give 4.46 g
  6. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-8b7f1ccd100e4a38a0433fc77f191a9b
Source dataset
uspto-grants-1981_04
Patent number
US04263309

Reaction notes

Loading…