(7-Benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amine → 6-benzyloxy-N4-[5-(methylthio)pentyl]quinoline-3,4-diamine

HRID 2383145Notes

Reaction equation

HRID 2383145 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([N+:19]([O-])=O)=[C:12]2[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C=C2C(C(NCCOC3C=CC=CC=3)=C([N+]([O-])=O)C=N2)=CC=1)C1C=CC=CC=1>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([NH2:19])=[C:12]2[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28][CH3:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 67050949(7-Benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amineHCID 670510536-benzyloxy-N-[5-(methylthio)pentyl]-3-nitroquinolin-4-amine

Product 1

HCID 670509646-benzyloxy-N4-[5-(methylthio)pentyl]quinoline-3,4-diamine

Procedure

A modification of the general method described in Part B of Example 46 was followed using 6-benzyloxy-N-[5-(methylthio)pentyl]-3-nitroquinolin-4-amine (5.1 g, 12 mmol) in lieu of (7-benzyloxy-3-nitro-quinolin-4-yl)-(2-phenoxyethyl)amine. The reaction was maintained under hydrogen pressure (49 psi, 3.4×105 Pa) for three hours. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with methanol (100 mL) and chloroform (50 mL). The filtrate was concentrated under reduced pressure to provide 6-benzyloxy-N4-[5-(methylthio)pentyl]quinoline-3,4-diamine as a yellow oil, which was used without purification.

Workup

  1. temperatureThe reaction was maintained under hydrogen pressure (49 psi, 3.4×105 Pa) for three hours
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was washed with methanol (100 mL) and chloroform (50 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b29e1d09064d43d3b3543c74f0f4ee58
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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