4-(6-Chloro-2,3-dihydro-indol-1-yl)-7-nitro-quinazoline hydrochloride → N-[4-(6-Chloro-2,3-dihydro-indol-1-yl)-quinazolin-7-yl]-hydroxylamine

HRID 1597989Notes

Reaction equation

HRID 1597989 reaction equation
Cl.[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][N:9]2[C:12]2[C:21]3[C:16](=[CH:17][C:18]([N+:22]([O-])=[O:23])=[CH:19][CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:5][CH:4]=1>CO.[Pd]>[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][N:9]2[C:12]2[C:21]3[C:16](=[CH:17][C:18]([NH:22][OH:23])=[CH:19][CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 189328314-(6-Chloro-2,3-dihydro-indol-1-yl)-7-nitro-quinazoline hydrochloride

Product 1

HCID 18932730N-[4-(6-Chloro-2,3-dihydro-indol-1-yl)-quinazolin-7-yl]-hydroxylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(6-Chloro-2,3-dihydro-indol-1-yl)-7-nitro-quinazoline hydrochloride (2.90 g, 7.98 mmol) was dissolved in 700 mL methanol and hydrogenated with 10% palladium on carbon (0.50 g) for 10 minutes at 3 atm. Reaction mixture was filtered through celite and diluted with 1.5 L diethyl ether. Product was filtered and dried under vacuum to give bright yellow solid, 2.23 g (80%):M.P. 262°-263° C. (dec); GC-MS: 313 (M+), 315 (M+ +2); Calc. C16H13ClN4O.HCl: C,55.03; H,4.04; N,16.04; Found: C,55.18; H,4.28; N,16.13.

Workup

  1. customReaction mixture
  2. filtrationwas filtered through celite
  3. additiondiluted with 1.5 L diethyl ether
  4. filtrationProduct was filtered
  5. customdried under vacuum
  6. customto give bright yellow solid, 2.23 g (80%)

Sources & evidence

ORD record
ord-6b5381db8359443fbcfc4ba396619402
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

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