Dimethylformamide → HCID 58980862, compound

HRID 1181379Notes

Reaction equation

HRID 1181379 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[O:14][CH3:15].[CH2:16]([N:18](CC)[CH2:19][CH3:20])[CH3:17].CN(C=[O:27])C>CCOC(C)=O>[CH3:15][O:14][C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][N:18]1[CH2:19][CH2:20][CH:17]([OH:27])[CH2:16]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 129372541-(2-Bromoethoxy)2-methoxy-4-nitrobenzene

Product 1

HCID 58980862HCID 58980862, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

1-(2-Bromoethoxy)2-methoxy-4-nitrobenzene (0.756 g, 2.7395 mmol) 3-pyrrolidinol (0.477 g, 5.479 mmol) and triethylamine (0.554 g, 5.479 mmol) were combined in DMF (10 mL) and heated to 80° C. The reaction was stirred for 2 h. Cooled to RT and diluted with EtOAc (100 mL) and washed with water (2×100 mL). The organics were dried over MgSO4, filtered and concentrated to afford 0.3967 g (1.407 mmol, 51%) of the desired product as a dark brown oil. 1H NMR (CDCl3) δ 7.90 (d, 1H, J=9.0 Hz), 7.75 (s, 1H), 6.93 (d, 1H, J=9.0 Hz), 4.38 (m, 1H), 4.24 (t, 2H, J=6.2 Hz), 3.95 (s, 3H), 3.2-3.0 (m, 4H), 3.0-2.90 (m, 1H), 2.8-2.70 (m, 1H), 2.60-2.50 (m, 1H), 2.30-2.20 (m, 1H), 1.85-1.75 (m, 1H).

Workup

  1. temperatureCooled to RT
  2. washwashed with water (2×100 mL)
  3. dry with materialThe organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ceeaa63b14c04b1d8cef824d4d87ecb2
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

Loading…