Methanol → HCID 18925028, compound

HRID 1288895Notes

Reaction equation

HRID 1288895 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[CH:21])[CH:15]=3)=[N:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[N+:22]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].CO>C(O)=O>[ClH:2].[NH2:22][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[Cl:2])[N:10]=[CH:9][N:8]=[C:7]2[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[CH:21])[CH:15]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24489Sodium DithioniteHCID 18925030HCID 18925030, compound

Product 1

HCID 18925028HCID 18925028, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

(7-Chloro-6-nitro-quinazolin-4-yl)-(3-ethynyl-phenyl)-amine hydrochloride (166 mg, 0.295 mmol) and sodium dithionite (207 mg, 1.19 mmol) were stirred in 1.5 mL of formic acid for 4 hours at room temperature. 45 mL of methanol were added to the reaction mixture which was set aside for 16 hours at room temperature. The precipitate thus obtained was filtered, triturated with 3% sodium bicarbonate for 0.5 hours and refiltered. The solid was dissolved in 20 mL of 1N HCl in methanol and precipitated with 200 mL of ethyl ether. This was filtered and dried in vacuo at 70° C. to afford the title product, 72 mg (83%); mp 260°-265° C.

Workup

  1. customThe precipitate thus obtained
  2. filtrationwas filtered
  3. customtriturated with 3% sodium bicarbonate for 0.5 hours
  4. dissolutionThe solid was dissolved in 20 mL of 1N HCl in methanol
  5. customprecipitated with 200 mL of ethyl ether
  6. filtrationThis was filtered
  7. customdried in vacuo at 70° C.

Sources & evidence

ORD record
ord-fd2f1975bbc34651b950dc9ecbf69662
Source dataset
uspto-grants-1998_05
Patent number
US05747498

Reaction notes

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