(6-nitro-quinolin-2-yl)-(R)-indan-1-yl-amine → (R)-N2-Indan-1-yl-quinoline-2,6-diamine

HRID 1931483Notes

Reaction equation

HRID 1931483 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([NH:14][C@H:15]1[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16]1)[CH:8]=[CH:7]2)([O-])=O>C(O)C.O.[Pt]=O>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([NH:14][C@H:15]1[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16]1)[CH:8]=[CH:7]2

Participants

4

Reactant 1

HCID 57860965(6-nitro-quinolin-2-yl)-(R)-indan-1-yl-amine

Product 1

HCID 57860958(R)-N2-Indan-1-yl-quinoline-2,6-diamine

Reagents, catalysts & solvents 2

HCID 86587499Platinum oxide monohydrateCatalystHCID 702EthanolSolvent

Procedure

(6-Nitro-quinolin-2-yl)-(R)-indan-1-yl-amine (0.37 g, 1.2 mmol) was dissolved in ethanol (15 mL). Platinum oxide hydrate (9 mg) was added and the mixture stirred for 4 h at ambient temperature under an atmosphere of hydrogen. The reaction mixture was filtered and evaporated and the residue was subjected to column chromatography (silica gel, heptane, ethyl acetate 1:0=>6:4). (6-Amino-quinolin-2-yl)-(R)-indan-1-yl-amine was isolated as a yellow foam (0.22 g, 66%); MS 276.5 [(M+H)+].

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-96ad61728e5b4edc9b7b2c17936e1d95
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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