Aniline → HCID 56926092, compound

HRID 2175458Notes

Reaction equation

HRID 2175458 reaction equation
[CH3:1][C:2]1([CH3:14])[O:13][C:6]2=[N:7][CH:8]=[C:9]([CH:11]=O)[CH:10]=[C:5]2[CH:4]=[CH:3]1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH3-]C#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[CH3:1][C:2]1([CH3:14])[O:13][C:6]2=[N:7][CH:8]=[C:9]([CH2:11][NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:10]=[C:5]2[CH:4]=[CH:3]1

Participants

6

Reactant 3

HCID 6115AnilineHCID 5003444Sodium cyanoborohydrideHCID 56925646HCID 56925646, compound

Product 1

HCID 56926092HCID 56926092, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2,2-dimethyl-2H-pyrano[2,3-b]pyridine-6-carbaldehyde 18 (20 mg, 0.106 mg) in methanol (1 ml) was added aniline (0.01 mL, 0.12 mmol), NaCNBH3 (13 mg, 0.212 mmol) and ZnCl2 (29 mg, 0.212 mmol). The reaction was stirred for 30 minutes after which the solvent was removed by rotary evaporation and the 1M NaOH added to the residue, extracted with DCM, dried over MgSO4 and concentrated in vacuo. Purified by column chromatography (3:1 Hx/EtOAc) to give a white solid 20 mg (72%). 1H NMR (CDCl3) δ 8.01 (s, 1H), 7.29 (s, 1H), 7.26-7.16 (m, 2H), 6.74 (t, J=7.2 Hz, 1H), 6.63 (d, J=8.0 Hz, 1H), 6.26 (d, J=9.6 Hz, 1H), 5.67 (d, J=9.6 Hz, 1H), 4.21 (s, 2H), 1.51 ppm (s, 6H). 13C NMR (CDCl3) δ 159.6, 147.8, 146.4, 133.8, 132.2, 129.3, 128.4, 120.9, 118.0, 115.4, 113.0, 79.2, 45.4, 28.8 ppm. HRMS (ESI) m/z calcd for C11H11NO2 [(M+H)+] 190.0868. found: 190.0870.

Workup

  1. customwas removed by rotary evaporation
  2. additionthe 1M NaOH added to the residue
  3. extractionextracted with DCM
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurified by column chromatography (3:1 Hx/EtOAc)

Sources & evidence

ORD record
ord-2458b7806a984370855d496a439e0840
Source dataset
uspto-grants-2015_06
Patent number
US09062072B2

Reaction notes

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