HCID 19101019, compound → HCID 53683293, compound

HRID 1198641Notes

Reaction equation

HRID 1198641 reaction equation
[NH2:1][C:2]1[O:7][C:6]2[C:8]3[C:13]([CH:14]=[CH:15][C:5]=2[CH:4]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([Cl:23])[CH:17]=2)[C:3]=1[C:24]#[N:25])=[CH:12][CH:11]=[CH:10][CH:9]=3>C(OCC)(OCC)OCC>[Cl:23][C:18]1[CH:17]=[C:16]([CH:4]2[C:3]([C:24]#[N:25])=[C:2]([N:1]=[CH:2][O:7][CH2:6][CH3:5])[O:7][C:6]3[C:8]4[C:13]([CH:14]=[CH:15][C:5]2=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH:21]=[CH:20][C:19]=1[F:22]

Participants

3

Reactant 1

HCID 19101019HCID 19101019, compound

Product 1

HCID 53683293HCID 53683293, compound

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

2-Amino 4 (3-chloro-4-fluorophenyl)-4H-naphtho[1,2-b]pyran-3-carbonitrile (3.12 g) was heated, under reflux, in triethyl orthoformate (40 ml) for 24 hours. A fraction coming over at 80° to 140° C. was distilled off and more triethyl orthofomate (40 ml) was added, and the refluxing was continued for a further 24 hours. The solution was evaporated to dryness. The gummy residue was dissolved in chloroform and passed through a column of `flash` silica using 30% hexane in chloroform as eluant. The fractions containing product were bulked, evaporated and triturated with ethyl acetate to give white crystals of 4-(3-chloro-4-fluorophenyl)-2-ethoxymethyleneamino-4H-naphtho[1,2-b]pyran-3-carbonitrile, m.p. 146°-148° C.

Workup

  1. customcoming over at 80° to 140° C.
  2. distillationwas distilled off
  3. additionmore triethyl orthofomate (40 ml) was added
  4. customThe solution was evaporated to dryness
  5. dissolutionThe gummy residue was dissolved in chloroform
  6. additionThe fractions containing product
  7. customevaporated
  8. customtriturated with ethyl acetate

Sources & evidence

ORD record
ord-080dad0257974b0ea29536bcf0e33561
Source dataset
uspto-grants-1994_01
Patent number
US05281619

Reaction notes

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