Triethylamine → HCID 19972641, compound

HRID 2400167Notes

Reaction equation

HRID 2400167 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[CH:5]([C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1)=O.Cl.CN.C(N(CC)CC)C>CO.[Cl-].[Zn+2].[Cl-]>[CH3:1][NH:2][CH2:5][C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 19972556HCID 19972556, compound

Product 1

HCID 19972641HCID 19972641, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 15.1 g of anhydrous zinc chloride and 14.5 g of sodium cyanoborohydride in 400 ml of anhydrous methanol was added dropwise with stirring at 0° C. to a mixture of 58 g of 8-formyl-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran (prepared as described in Uneyama, K. et al., Bull. Chem. Soc. Jap. 58:2361 (1985)), 60.7 g of methylamine hydrochloride and 125 ml of triethylamine in 600 ml of anhydrous methanol. After stirring for 5 hours at 20°-25° C., the solvent was evaporated off in vacuo and the residue was taken up in 200 ml of water and collected by suction filtration. The crude product was dissolved in aqueous acetic acid, washed with ethyl acetate and reprecipitated by the addition of a 6N sodium hydroxide solution. 49 g of the title compound was obtained, with a melting point of 97°-99° C., after crystallization from 75% ethanol.

Workup

  1. customthe solvent was evaporated off in vacuo
  2. filtrationcollected by suction filtration
  3. dissolutionThe crude product was dissolved in aqueous acetic acid
  4. washwashed with ethyl acetate
  5. customreprecipitated by the addition of a 6N sodium hydroxide solution

Sources & evidence

ORD record
ord-97ccbb85183c4120b161edded8f8ae4a
Source dataset
uspto-grants-1995_09
Patent number
US05453518

Reaction notes

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