2-Hydrazino-3-(3-isopropoxy-phenyl)-3H-quinazolin-4-one → 4(3H)-Quinazolinone, 2-amino-3-[3-(1-methylethoxy)phenyl]-

HRID 362602Notes

Reaction equation

HRID 362602 reaction equation
[NH:1]([C:3]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH:20]([CH3:22])[CH3:21])[CH:14]=2)[C:11](=[O:23])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)N.[H][H]>CO.C1COCC1.[Ni]>[NH2:1][C:3]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH:20]([CH3:21])[CH3:22])[CH:14]=2)[C:11](=[O:23])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

5

Reactant 2

HCID 106148972-Hydrazino-3-(3-isopropoxy-phenyl)-3H-quinazolin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 108277054(3H)-Quinazolinone, 2-amino-3-[3-(1-methylethoxy)phenyl]-

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 2-Hydrazino-3-(3-isopropoxy-phenyl)-3H-quinazolin-4-one (2.5g, 8.0 mmol) in 100 mL methanol-THF (1:1) was treated with Raney Ni (2.0), and resulting suspension was subjected to atmosphere of hydrogen at 52.0 psi for 30 hours with agitation at temperature of 50° C. An additional 1.0 g of Raney Ni was added and reaction was continued for additional 40 hours at 50° C. The mixture was then filtered through celite, and the solvent was removed in vacuo to give the title compound as a reddish yellow solid. This crude product was then titurated with ethyl acetate and hexane to isolate 1.85 g (78%) product as a light yellow solid, mp 130°-133° C.

Workup

  1. customresulting suspension
  2. customreaction
  3. filtrationThe mixture was then filtered through celite
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ac755582ab2d4119bfda7bfda5dd3d48
Source dataset
uspto-grants-1999_02
Patent number
US05869665

Reaction notes

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