Sodium Bicarbonate → HCID 9878158, compound

HRID 1826989Notes

Reaction equation

HRID 1826989 reaction equation
C([BH3-])#N.[Na+].[NH2:5][C:6]1[C:15]([C:16]#[N:17])=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[NH2:5][C:6]1[NH:7][C:8]2[C:13]([CH:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]=1[C:16]#[N:17])=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride2×HCID 124729752-Amino-4-phenylquinoline-3-carbonitrile

Product 1

HCID 9878158HCID 9878158, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanoborohydride (10 mg) was added to 2-amino-4-phenylquinoline-3-carbonitrile (5 mg) in solution in acetic acid (0.25 mL). After stirring 85 min at room temperature, there was no more change in TLC, so sodium cyanoborohydride (15 mg) was further added. The reaction mixture was allowed to stir for another 20 min, then was neutralized with saturated sodium bicarbonate solution and extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution and dried. The crude obtained after removing the solvent was passed through a bond-elute (4:1 to 7:3 hexane-ethyl acetate) yielding 2 mg of 2-amino-3-cyano-4-phenyl-1,4-dihydroquinoline. 1H NMR (CD3OD): 7.22–7.26 (m, 2H), 7.12–7.19 (m, 3H), 7.07 (dt, J=7.8, 1.6 Hz, 1H), 6.92 (finely split doublet, J=7.8 Hz, 1H), 6.82 (dt, J=7.6, 1.2 Hz, 1H), 6.77 (dd, J=8.1, 1.2 Hz, 1H), 4.76 (s, 1H).

Workup

  1. additionwas further added
  2. stirringto stir for another 20 min
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated sodium chloride solution
  5. customdried
  6. customThe crude obtained
  7. customafter removing the solvent
  8. washa bond-elute (4:1 to 7:3 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-616c30c7c2484bd1bfda240ab00eea73
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

Loading…