Ammonium Chloride → HCID 21098395, compound

HRID 1351168Notes

Reaction equation

HRID 1351168 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:22]([O-])=O)=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH4+].[Cl-]>CO.O.C(Cl)(Cl)Cl.[Zn]>[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]2[N:9]=[CH:8][N:7]=[C:6]([NH:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:5]=2[C:4]=1[NH2:22]

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 21098394HCID 21098394, compound

Product 1

HCID 21098395HCID 21098395, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of (6,7-dimethoxy-5-nitro-quinazolin-4-yl)-phenyl-amine (1.0 g, 3.14 mmol) (from Example 1, Step B, supra), NH4Cl (1.7 g, 31.4 mmol) in MeOH, H2O and CHCl3 (40 mL, 2:1:1) was added Zn powder (2.0 g, 31.4 mmol) (Aldrich). The reaction mixture was stirred at room temperature for 1 hour. The mixture was then filtered, the filtrate was concentrated and then extracted with chloroform (100 mL). The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by chromatography using EtOAc/CH2Cl2 (1:1) as eluent to give the desired 6,7-dimethoxy-N 4-phenyl-quinazoline-4,5-diamine as a yellow gum. (Yield 0.5 g, 54%).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated
  3. extractionextracted with chloroform (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-cfb297ba46c74180bd001681bce3c97a
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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