HCID 10559687, compound → HCID 23122564, compound

HRID 968492Notes

Reaction equation

HRID 968492 reaction equation
[N+:1]([C:4]1[C:5]([NH2:14])=[N:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1)([O-])=O.[H][H]>CO>[N:6]1[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=[C:4]([NH2:1])[C:5]=1[NH2:14]

Participants

4

Reactant 2

HCID 10559687HCID 10559687, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23122564HCID 23122564, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of intermediate (9) (0.0658 mol) in NH3/CH3OH 7N (60 ml) was stirred at 120° C. for 12 hours in an autoclave. The solvent was evaporated till dryness. The residue was taken up in 2-propanone. The precipitate was filtered off and dried, yielding 8.6 g 5,6,7,8-tetrahydro-3-nitro-2-quinolinamine (intermediate 10). d) A mixture of intermediate (10) (0.031 mol) in methanol (100 ml) was hydrogenated at room temperature under a 3.105 Pa (3 bar) pressure for 30 minutes in a Parr apparatus. After uptake of hydrogen (3 equivalents), the catalyst was filtered through celite, rinced with methanol and the filtrate was evaporated till dryness. The product was used with further purification, yielding 5.07 g 5,6,7,8-tetrahydro-2,3-quinolinediamine (intermediate 11).

Workup

  1. customthe filtrate was evaporated till dryness
  2. customThe product was used with further purification

Sources & evidence

ORD record
ord-1236e7f96c6c492aafffbdef67fd2e75
Source dataset
uspto-grants-2007_12
Patent number
US07304052B2

Reaction notes

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