Cyclohexanecarboxaldehyde → HCID 44450275, compound

HRID 1944526Notes

Reaction equation

HRID 1944526 reaction equation
[CH3:1][NH:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([NH:9][C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:8])=[CH:5][CH:4]=1.[CH2:22]1[CH2:27][CH2:26][CH:25](C=O)[CH2:24][CH2:23]1.[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C>ClCCCl>[CH:22]1([CH2:1][N:2]([CH3:30])[C:3]2[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]3[CH:11]=[N:12][C:13]4[C:18]([CH:19]=3)=[CH:17][CH:16]=[CH:15][CH:14]=4)=[O:8])=[CH:20][CH:21]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 59859876HCID 59859876, compound

Product 1

HCID 44450275HCID 44450275, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 4-methylamino-N-quinolin-3-yl-benzamide (0.075 g, 0.27 mmol), cyclohexylcarboxaldehyde (0.049 mL, 0.405 mmol) and tetramethylammonium triacetoxyborohydride (0.213 g, 0.81 mmol) in 1,2-dichloroethane was heated to 85° C. in a sealed tube for 18 hours. The solution was cooled to room temperature and washed with a solution of ammonium hydroxide in water. The product was preabsorbed on silica gel and purified by flash chromatography, using ethyl acetate/hexane (1/1) as the eluant, to give the product as a colorless solid, 0.051 g (51%). MS: m/z 374 (MH+). 1H NMR (DMSO-d6): 0.90-1.05 (m, 2 H), 1.10-1.23 (m, 3 H), 1.58-1.77 (m, 6 H), 3.02 (s, 3 H), 3.27 (d, 2 H), 6.77 (d, 2 H), 7.54-7.67 (m, 2 H), 7.91 (d, 2 H) superimposed on 7.95 (t, 2 H), 8.81 (d, 1 H), 9.15 (d, 1 H) and 10.28 (s, 1 H).

Workup

  1. washwashed with a solution of ammonium hydroxide in water
  2. customThe product was preabsorbed on silica gel
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-a1568830f6de46d3bea5565b9f1eb58a
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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