Hydrochloric Acid → HCID 19101024, compound

HRID 1198642Notes

Reaction equation

HRID 1198642 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]([C:14]#[N:15])=[C:12]([N:16]=[CH:17]OCC)[O:11][C:10]3[C:21]4[C:26]([CH:27]=[CH:28][C:9]2=3)=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:4][C:3]=1[N+:29]([O-:31])=[O:30].[BH4-].[Na+].Cl.O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]([C:14]#[N:15])=[C:12]([NH:16][CH3:17])[O:11][C:10]3[C:21]4[C:26]([CH:27]=[CH:28][C:9]2=3)=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:4][C:3]=1[N+:29]([O-:31])=[O:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 53716136HCID 53716136, compound

Product 1

HCID 19101024HCID 19101024, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Chloro-3-nitrophenyl)-2-ethoxymethyleneamino-4H-naphtho[1,2-b]pyran-3-carbonitrile (4.3 g) was dissolved in tetrahydrofuran (70 ml), and to this solution, with stirring, was added sodium borohydride (2.7 g), in portions. After one hour the suspension was cooled in ice-water and 1 molar hydrochloric acid (20 ml) was added dropwise, followed by water (200 ml). A yellow product was filtered off, washed with water and dried. This material was dissolved in hot chloroform and passed down a chloroform--`flash silica` column. Fractions containing product were bulked, evaporated to dryness, and triturated with ether to give 4-(4-chloro-3-nitrophenyl)-2-methylamino-4H-naphtho[1,2-b]pyran-3-carbonitrile, m.p. 278.5°-279° C.

Workup

  1. filtrationA yellow product was filtered off
  2. washwashed with water
  3. customdried
  4. dissolutionThis material was dissolved in hot chloroform
  5. additionFractions containing product
  6. customevaporated to dryness
  7. customtriturated with ether

Sources & evidence

ORD record
ord-b6ceb4b1ce5248919803c91be6fd463d
Source dataset
uspto-grants-1994_01
Patent number
US05281619

Reaction notes

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