Ethanol → 7-(Benzylamino)-4-methyl-2H-1-benzopyran-2-one

HRID 2050338Notes

Reaction equation

HRID 2050338 reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](OCC)(=[O:21])[CH2:17][C:18]([CH3:20])=O.C(O)C>O.Cl.[Cl-].[Zn+2].[Cl-]>[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]2[C:12]([C:18]([CH3:20])=[CH:17][C:16](=[O:21])[O:15]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 702EthanolHCID 8868Ethyl AcetoacetateHCID 12713133HCID 12713133, compound

Product 1

HCID 203425797-(Benzylamino)-4-methyl-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

7-Benzylamino-4-methylcoumarin was synthesized from 3-benzylaminophenol and ethyl acetoacetate by the usual Peckmann reaction (anhydrous zinc chloride, absolute ethanol). Recrystallization from ethanol gave flat needles, m.p. 174.5°-175.5° C. The fluorescence maximum in water was 455 nm (excited 355 nm), in 10-2N HCl 458 nm. 1H nmr (60 MHz, CDCl3), δ2.36 (s, 3H, C--CH3), 4.45 (d, 2H, --CH2NH--, J=~5.5 Hz, collapses to a singlet when D2O added), 4.7-5 (1H, NH), 6.03 (s, 1H, H3), 6.57 (d, 1H H8), 6.63 (dd, 1H, H6, J56 =~9 Hz, J68 =~2 Hz), 7.45 (s, 5H, C6H5), 7.45 (d, 1H, H5, J56 =~9 Hz).

Workup

  1. customRecrystallization from ethanol
  2. customgave flat needles, m.p. 174.5°-175.5° C

Sources & evidence

ORD record
ord-1778b46fd8074737a10e5d34a03796d2
Source dataset
uspto-grants-1980_04
Patent number
US04200753

Reaction notes

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