Pentylamine → HCID 57850035, compound

HRID 736594Notes

Reaction equation

HRID 736594 reaction equation
[CH:1]([C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:12][CH:13]=O)=[O:2].[CH2:15]([NH2:20])[CH2:16][CH2:17][CH2:18][CH3:19]>CCO>[OH:2][CH:1]1[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:9]([O-:11])=[O:10])[N:12]=[CH:13][N:20]1[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 8060PentylamineHCID 57850033HCID 57850033, compound

Product 1

HCID 57850035HCID 57850035, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(2-Formyl-3-nitrophenyl)formamide (5a, 20.0 g, 103 mmol) and n-pentylamine (23.9 ml, 206 mmol) were dissolved in EtOH (240 ml) and the mixture stirred at room temperature for 3 h. After the mixture was concentrated under reduced pressure, EtOAc (100 ml) was added to the residue, and the generating yellow crystal was collected by filtration. The crystal was washed with EtOAc and dried under vacuum to obtain 4-hydroxy-5-nitro-3-pentyl-3,4-dihydroquinazoline (6a, 19.6 g, 72%); 1H NMR (270 MHz) δ (CDCl3) 0.91 (t, J=6.7 Hz, 3H), 1.26-1.38 (m, 4H), 1.67-1.78 (m, 2H), 3.21 (dt, J=13.9 and 7.9 Hz, 1H), 3.77 (ddd, J=6.3, 7.6 and 13.9 Hz, 1H), 6.57 (s, 1H), 6.90 (s, 1H), 7.30-7.41 (m, 2H), 7.80 (dd, J=1.7 and 7.6 hz, 1H); MS (ES) m/z 264 (M++1).

Workup

  1. concentrationAfter the mixture was concentrated under reduced pressure, EtOAc (100 ml)
  2. additionwas added to the residue
  3. filtrationthe generating yellow crystal was collected by filtration
  4. washThe crystal was washed with EtOAc
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0fb12cc919924fedbd60820d01a0febf
Source dataset
uspto-grants-2009_09
Patent number
US07595400B2

Reaction notes

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