Sulfuric Acid → 1,2,3,4-Tetrahydroquinoline-5,6-diamine

HRID 48214Notes

Reaction equation

HRID 48214 reaction equation
[N:1]1[C:10]2[C:5](=[C:6]([NH2:12])[C:7]([NH2:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O>CO.[Pt]=O>[NH2:12][C:6]1[C:7]([NH2:11])=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][CH2:2][NH:1]2

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 426874Quinoline-5,6-diamine

Product 1

HCID 227424661,2,3,4-Tetrahydroquinoline-5,6-diamine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)Catalyst2×HCID 887MethanolSolvent

Procedure

A solution of 5,6-quinolinediamine (12.5 g, 0.065 mol) and sulfuric acid (8 mL) in methanol (250 mL) was treated with platinum oxide (1 g) in a Parr apparatus under hydrogen for 16 hours. An additional 1 g portion of platinum oxide was added and hydrogenation continued for 44 hours additional. Standard work-up gave the 5,6-diaminotetrahydroquinoline.

Sources & evidence

ORD record
ord-71bc07ae0cd34c7fa0e0d08e19635dce
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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