Hydrochloric Acid → HCID 67202052, compound

HRID 547572Notes

Reaction equation

HRID 547572 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:26])[C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.CCO.[ClH:30]>[Fe].O>[ClH:30].[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([S:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=3)=[CH:14][CH:13]=2)=[O:26])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 59457996HCID 59457996, compound

Product 1

HCID 67202052HCID 67202052, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Nitro compound 10 (0.83 g, 2.07 mmol) was suspended in 2:1 EtOH:H2O (100 mL) and the resulting suspension brought to reflux. To this mixture was sequentially added Fe dust (0.54 g, 9.59 mmol) and c.HCl (2 mL), and the resulting dark orange suspension was refluxed for 1 h. After this time, the resulting yellow suspension was filtered hot through a pad of Celite, and the solvent removed under reduced pressure. The residue was re-suspended on H2O, to which was added a quantity of Celite, and the resulting suspension was stirred overnight. After this time, the suspension was filtered through a pad of Celite, and solvent was removed under reduced pressure to afford crude amine 11 as an amorphous off-white solid (0.65 g, 93%), which was used without further purification. 1H NMR [(CD3)2SO]: δ 9.98 (s, 1H, ArC(O)NHAr), 7.91 (ddd, J=9.40, 4.48, 2.58 Hz, 2H, ArH), 7.72 (m, 3H, ArH), 7.48 (ddd, J=9.37, 4.39, 2.55 Hz, 2H, ArH), 6.61 (d, J=7.85 Hz, 2H, ArH), 6.18 (dd, J=5.46, 1.68 Hz, 1H, ArH), 5.82 (d, J=1.36 Hz, 1H, ArH), 6.01 (br s, 2H, ArNH2), 5.82 (br s, 2H, ArNH2); HRMS: Calc. for C18H17N4OS (MH+) m/z 337.1123, found 337.1126.

Workup

  1. temperatureto reflux
  2. filtrationAfter this time, the resulting yellow suspension was filtered hot through a pad of Celite
  3. customthe solvent removed under reduced pressure
  4. additionwas added a quantity of Celite
  5. filtrationAfter this time, the suspension was filtered through a pad of Celite, and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-bb556650061c4076bc3defc89d38029e
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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