Sodium Bicarbonate → HCID 22464070, compound

HRID 1935623Notes

Reaction equation

HRID 1935623 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14]C)=[O:12])=[CH:5]2.[Mg].C([O-])(O)=O.[Na+]>>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]([C:11]([O:13][CH3:14])=[O:12])[CH2:5]2

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 5462224MagnesiumHCID 10726872Ethyl 5-amino-1H-indole-2-carboxylate

Product 1

HCID 22464070HCID 22464070, compoundYield 89.2%

Conditions

Temperature
23.5 °C

Procedure

A stirred solution of the product from Step 1 (8.81 g, 0.0431 mol), under nitrogen, is treated with magnesium turnings (3.3 g) and kept for about 10 min when the solution became cloudy and an exothermic reaction began. It is stirred for an additional 5 min (23-24° C.), cooled to 6-7° C. in a water bath and kept for 5.5 h. This mixture is kept at 8° C. for 18 h, acidified to pH 3 with ice cold 6N HCl, neutralized with saturated NaHCO3, and extracted with EtOAc. The extracts are washed with water, dried (Na2SO4) and concentrated in vacuo to give 7.39 g of the titled product: MS (ES) m/z 193 (M+H+), 215 (17+Na+); 1H NMR (300 MHz, CDCl3); δ3.28 (m, 2H), 3.52 (broad s, 3H), 374 (s, 3H), 4.33 (q, 1H), 6.46 (m, 1H), 6.56 (m, 2H).

Workup

  1. customan exothermic reaction
  2. temperaturecooled to 6-7° C. in a water bath
  3. waitkept for 5.5 h
  4. waitThis mixture is kept at 8° C. for 18 h
  5. extractionextracted with EtOAc
  6. washThe extracts are washed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72fe3c8d5af04987b54572bad925bce0
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

Loading…