Hydrochloric Acid → HCID 19962752, compound

HRID 52013Notes

Reaction equation

HRID 52013 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:20]=[CH:19][C:18]3[NH:17][C:16]([CH3:21])=[C:15]([N+:22]([O-])=O)[C:14]=3[C:13]=2[C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26])[N:4]=1.Cl.[Sn]>CO>[NH2:22][C:15]1[C:14]2[C:13]([C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26])=[C:12]([O:11][C:5]3[N:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[N:4]=3)[CH:20]=[CH:19][C:18]=2[NH:17][C:16]=1[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 19962765HCID 19962765, compound

Product 1

HCID 19962752HCID 19962752, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.4 g of allyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methyl-3-nitroindol-4-carboxylate was dissolved in 50 ml of methanol, and 5 ml of concentrated hydrochloric acid was added thereto. Then, 4.9 g of tin powder was gradually added at room temperature. Them, the mixture was stirred at room temperature for 12 hours. The solid was filtered off, and then residue was concentrated under reduced pressure and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2.5 g (yield: 79%) of the desired product. mp: 132°-135° C.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationresidue was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue obtained by concentration under reduced pressure
  7. customwas crystallized from isopropyl ether

Sources & evidence

ORD record
ord-172b663c480f428491802387607eff65
Source dataset
uspto-grants-1997_04
Patent number
US05616537

Reaction notes

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