Hydrochloric Acid → HCID 22452057, compound

HRID 2185655Notes

Reaction equation

HRID 2185655 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:24][CH2:25][CH2:26][CH2:27][O:28]C4CCCCO4)=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[F:9]>CO>[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:24][CH2:25][CH2:26][CH2:27][OH:28])=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[F:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22452055HCID 22452055, compound

Product 1

HCID 22452057HCID 22452057, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

3.00 ml of concentrated hydrochloric acid are added dropwise to 21.30 g of 4-[(3-chloro-4-fluoro-phenyl)amino]-7-[3-(tetrahydropyran-2-yloxy)-propyloxy]-6-nitro-quinazoline in 200 ml of methanol. A yellow precipitate is formed. The suspension is stirred for about another 3.5 hours at 50° C. For working up the methanol is distilled off in vacuo using a rotary evaporator. The residue is combined with ethyl acetate and some ice-water and made alkaline with sodium hydroxide solution. The organic phase is washed with water and saturated sodium chloride solution and left to stand overnight at ambient temperature, whereupon a yellow precipitate is formed. This is suction filtered, washed with ethyl acetate and dried. The filtrate is evaporated down and the evaporation residue is recrystallised from ethyl acetate. The crystals thus obtained are combined with the previously suction filtered precipitate and again recrystallised from ethyl acetate. The desired product is obtained in the form of slightly yellowish crystals.

Workup

  1. customA yellow precipitate is formed
  2. distillationis distilled off in vacuo
  3. customa rotary evaporator
  4. washThe organic phase is washed with water and saturated sodium chloride solution
  5. waitleft
  6. waitto stand overnight at ambient temperature, whereupon a yellow precipitate
  7. customis formed
  8. filtrationThis is suction filtered
  9. washwashed with ethyl acetate
  10. customdried
  11. customThe filtrate is evaporated down
  12. customthe evaporation residue is recrystallised from ethyl acetate
  13. customThe crystals thus obtained
  14. customagain recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-b124ad7cfd1f42d6bc114f2ac31627ee
Source dataset
uspto-grants-2002_06
Patent number
US06403580B1

Reaction notes

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