HCID 85439451, compound → HCID 59400117, compound

HRID 2389549Notes

Reaction equation

HRID 2389549 reaction equation
O[N:2]=[C:3]1[CH2:9][CH2:8][N:7]([S:10]([C:13]2[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C:6]2[CH:20]=[CH:21][CH:22]=[CH:23][C:5]=2[C:4]1=[O:24].[H][H]>CO>[NH2:2][CH:3]1[CH2:9][CH2:8][N:7]([S:10]([C:13]2[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C:6]2[CH:20]=[CH:21][CH:22]=[CH:23][C:5]=2[CH:4]1[OH:24]

Participants

4

Reactant 2

HCID 85439451HCID 85439451, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59400117HCID 59400117, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-(hydroxyimino)-1-tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one (7.0 g) in methanol (300 mL) Raney nickel (11.0 g) was added. The reaction mixture was stirred under 1 atmosphere of hydrogen gas for 15-16 h. The reaction mixture was filtered through celite, washed with methanol (150 mL×3) and evaporated under reduced pressure to give 4-amino-1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ol (7.2 g, 95%). 1H NMR: (400 MHz, CDCl3) δ: 7.67 (2H, d, J=8.0 Hz), 7.55 (1H, d, J=7.6 Hz), 7.42 (2H, d, J=7.6 Hz 7.32 (1H, t, J=7.2 Hz), 7.22 (1H, t, J=7.6 Hz), 7.04 (1H, d, J=7.6 Hz), 5.53 (1H, b), 4.08 (2H, d, J=8.0 Hz), 3.1 (1H, m), 2.4 (3H, s), 1.7 (3H, m).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed with methanol (150 mL×3)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8502d5af34d347658d7aae485971d9e7
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

Loading…