Water → Methyl 4-(7-cyanonaphth-1-ylmethyl)-3-methoxybenzoate

HRID 2371795Notes

Reaction equation

HRID 2371795 reaction equation
[C-:1]#[N:2].[Na+].F[B-](F)(F)F.[CH3:9][O:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([N+]#N)[CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[C:15]([O:32][CH3:33])[CH:14]=1)=[O:12].C(OCC)(=O)C.O>CN(C)C=O>[C:1]([C:27]1[CH:28]=[C:29]2[C:24]([CH:23]=[CH:22][CH:21]=[C:20]2[CH2:19][C:16]2[CH:17]=[CH:18][C:13]([C:11]([O:10][CH3:9])=[O:12])=[CH:14][C:15]=2[O:32][CH3:33])=[CH:25][CH:26]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 199063931-(4-Methoxycarbonyl-2-methoxyphenylmethyl)naphthalene-7-diazonium tetrafluoroborate

Product 1

HCID 19906375Methyl 4-(7-cyanonaphth-1-ylmethyl)-3-methoxybenzoateYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of cuprous cyanide (2.52 g), sodium cyanide (1.68 g), and dimethylformamide (50 ml, distilled over CaH2) was stirred for 1 h. The homogeneous solution was cooled to 0° C. and a solution of 1-(4-methoxycarbonyl-2-methoxyphenylmethyl)naphthalene-7-diazonium tetrafluoroborate (2.62 g), in dimethylformamide (12 ml, distilled over CaH2) was added. The reaction was stirred for 15 min at 0° C. and then at room temperature for 16 h. The mixture was added to ethyl acetate (200 ml) and water (300 ml) and filtered through diatomaceous earth with ethyl acetate washes. The organic layer was washed (water, brine), dried (MgSO4), and evaporated. Flash chromatography of the residue, eluting with methylene chloride, and trituration of the product with hot ether afforded methyl 4-(7-cyanonaphth-1-ylmethyl)-3-methoxybenzoate (1.04 g, 56%) as a pale yellow solid; mp 138.5°-139.5° C.; MS(CI), m/e=33Z(M+H).

Workup

  1. stirringThe reaction was stirred for 15 min at 0° C.
  2. waitat room temperature for 16 h
  3. filtrationfiltered through diatomaceous earth with ethyl acetate washes
  4. washThe organic layer was washed (water, brine)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. washFlash chromatography of the residue, eluting with methylene chloride, and trituration of the product with hot ether

Sources & evidence

ORD record
ord-d3e7d0cb01d04c7ea8922f446212c01c
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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