Ethanol → HCID 122449335, compound

HRID 1482725Notes

Reaction equation

HRID 1482725 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1.C(O)C.[H][H]>C(Cl)Cl.[Pd]>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 132191191-[(8-Bromooctyl)oxy]-4-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 122449335HCID 122449335, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

Into a glass hydrogenation vessel were added 1-(8-bromooctyloxy)-4-nitrobenzene (5.00 g, 15.1 mmol) and absolute ethanol (50 mL). Carefully, 10% Pd/C (0.5 g) was added, the vessel was charged with hydrogen (40 psi), and the mixture was shaken on a Pan hydrogenation apparatus. After 3 h the mixture was diluted with CH2Cl2 (25 mL), filtered through a Celite pad, and volatiles removed in vacuo to give 4.20 g (14.0 mmol, 93%), of as a pale pink solid, mp 61-63° C. This material was used without purification in the next reaction. 1H NMR (500 MHz, CDCl3) δ 1.27-1.44 (m, 8H), 1.75-1.84 (m, 4H), 3.39 (t, J=5.0 Hz, 2H), 3.89 (t, J=6.5 Hz, 2H), 6.77-6.88 (m, 2H); 13C NMR (125 MHz, CDCl3) δ 22.7, 25.9, 26.0, 28.1, 28.7, 29.2, 29.4, 31.8, 32.8, 34.0, 68.5, 115.7, 118.6, 135.2, 154.1; HRMS (ESI) calculated for C14H23BrNO [M+H]+ 300.0957, observed 300.0963.

Workup

  1. filtrationfiltered through a Celite pad, and volatiles
  2. customremoved in vacuo
  3. customto give 4.20 g (14.0 mmol, 93%)
  4. customThis material was used without purification in the next reaction

Sources & evidence

ORD record
ord-ff18a124126343538ab0a46a2ebf3090
Source dataset
uspto-grants-2016_08
Patent number
US09415110B1

Reaction notes

Loading…