Triethylamine → HCID 19972641, compound

HRID 1452286Notes

Reaction equation

HRID 1452286 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 aqueous 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 aqueous sodium hydroxide solution

Sources & evidence

ORD record
ord-e0a91c6b64e444de8a5b45b6db1819f5
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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