Hydrochloric Acid → HCID 54313644, compound

HRID 1597943Notes

Reaction equation

HRID 1597943 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N+:24]([O-])=O)[CH:22]=2)[CH2:17][CH2:16]1.Cl>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([NH2:24])[CH:22]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18932872HCID 18932872, compound

Product 1

HCID 54313644HCID 54313644, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6,7-Dimethoxy-4-(6-nitro-2,3-dihydro-indol-1-yl)-quinazoline (0.50 g, 1.42 mmol; from Example 26) in MeOH (10 mL) with conc. HCl (1 mL) was hydrogenated for 18 hours under 45 psi of H2(g) in the presence of 10% Pd-C (105 mg). Following filtration through a pad of Celite and concentration of the filtrate in vacuo, the residue was taken up in 10% i-PrOH/CHCl3 and the organic phase washed successively with saturated NaHCO3, 0.1M disodium EDTA, and brine. The organic solution was added over Na2SO4(s), filtered and concentrated in vacuo to afford the product as a yellow solid (423 mg; M.P. 215°-217.5° C.; LC-MS: 323 (MH+); anal. RP-HPLC RT: 3.10 min).

Workup

  1. filtrationfiltration through a pad of Celite and concentration of the filtrate in vacuo
  2. washthe organic phase washed successively with saturated NaHCO3, 0.1M disodium EDTA, and brine
  3. additionThe organic solution was added over Na2SO4(s)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-418645731b72417cba50a696bc4f04c2
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

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