N-(3-Bromophenyl)-6-nitroquinazolin-4-amine → N4-(3-Bromophenyl)quinazoline-4,6-diamine

HRID 430490Notes

Reaction equation

HRID 430490 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1>C(O)C.C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 5328041N-(3-Bromophenyl)-6-nitroquinazolin-4-amine

Product 1

HCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 34.5 g of N-(3-bromophenyl)-6-nitro-4-quinazolinamine and 16.8 g of iron powder in 150 ml of ethanol and 150 ml of glacial acetic acid was heated in an oil bath at 120° C. for 2 hours. After filtration of the solid, solid sodium carbonate was added to the filtrate giving a solid. This was filtered, and the solid was extracted with methanol. The extracts were treated with charcoal and evaporated to a solid. After washing the solid with ether 27.5 g of N-(3-bromophenyl)-4,6-quinazolindiamine was obtained: mass spectrum (m/e): 315.

Workup

  1. filtrationAfter filtration of the solid, solid sodium carbonate
  2. additionwas added to the filtrate
  3. customgiving a solid
  4. filtrationThis was filtered
  5. extractionthe solid was extracted with methanol
  6. additionThe extracts were treated with charcoal
  7. customevaporated to a solid
  8. washAfter washing the solid with ether 27.5 g of N-(3-bromophenyl)-4,6-quinazolindiamine
  9. customwas obtained

Sources & evidence

ORD record
ord-7e23f455b4d24ec0928e889d96c5e68e
Source dataset
uspto-grants-2001_11
Patent number
US06323209B1

Reaction notes

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