Toluene → HCID 86684832, compound

HRID 595141Notes

Reaction equation

HRID 595141 reaction equation
C([O-])(=O)C.[NH4+].[N+:6]([C:9]1[C:24]([C:25](=[O:27])[CH3:26])=[CH:23][C:12]2[O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][C:11]=2[CH:10]=1)([O-])=O.C1(C)C=CC=CC=1>[Fe].O>[NH2:6][C:9]1[C:24]([C:25](=[O:27])[CH3:26])=[CH:23][C:12]2[O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][C:11]=2[CH:10]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 517165Ammonium AcetateHCID 86684831HCID 86684831, compound

Product 1

HCID 86684832HCID 86684832, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A Mixture of iron powder (477 mmol, 27 g), ammonium acetate (500 mmol, 31 g), 1-(3-Nitro-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-ethanone (120 mmol, 36 g), toluene (500 ml) and water (500 ml) was refluxed overnight, or until completion. The mixture was filtered through celite and washed with EtOAc. The organic layer was washed with water and Sat. NaCl, dried over Na2SO4, and concentrated to afford the product, 90%. 1HNMR (400 MHz, DMSO) δ 7.82 (s, 1H), 7.61 (s, 1H), 5.45 (s, 2H), 4.35 (s, 4H), 3.87 (d, 4H), 3.62 (s, 4H), 2.71 (s, 3H). LC/MS Calcd for (M+H)+282.3. found 282.5.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe mixture was filtered through celite
  3. washwashed with EtOAc
  4. washThe organic layer was washed with water and Sat. NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford the product, 90%

Sources & evidence

ORD record
ord-3d4229a5da8b4b5aac9a007442a2b213
Source dataset
uspto-grants-2016_01
Patent number
US09242991B2

Reaction notes

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