Triethylamine → HCID 19972641, compound

HRID 1653790Notes

Reaction equation

HRID 1653790 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 78.8%

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 at 0° C. into a stirred mixture of 58.8 g of 8-formyl-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran, 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 re-precipitated by addition of cold 6N sodium hydroxide solution. 49 g of the title compound was obtained. m.p. 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. customre-precipitated by addition of cold 6N sodium hydroxide solution

Sources & evidence

ORD record
ord-6ff95784fd3f426b9c048cba6e06b730
Source dataset
uspto-grants-1995_04
Patent number
US05403842

Reaction notes

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