HCID 5156493, compound → HCID 10559687, compound

HRID 968491Notes

Reaction equation

HRID 968491 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[NH3:15].CO>>[N+:12]([C:11]1[C:2]([NH2:15])=[N:3][C:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1)([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 5156493HCID 5156493, compoundHCID 21705897Ammonia methanol

Product 1

HCID 10559687HCID 10559687, compound

Conditions

Temperature
120 °C

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 solvent was evaporated till dryness
  2. filtrationThe precipitate was filtered off
  3. customdried

Sources & evidence

ORD record
ord-3eacdbdeca0a4819ad0f2cb810565eeb
Source dataset
uspto-grants-2007_12
Patent number
US07304052B2

Reaction notes

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