Aniline → HCID 13564469, compound

HRID 1284559Notes

Reaction equation

HRID 1284559 reaction equation
[OH:1][C:2]1[C:3]([CH:12]=O)=[CH:4][C:5]2[O:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:11]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[OH:1][C:2]1[C:3]([CH2:12][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4][C:5]2[O:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 13560308HCID 13560308, compound

Product 1

HCID 13564469HCID 13564469, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-hydroxy-3,4-dihydrobenzopyran-7-carboxaldehyde (429 mg, 2.41 mmol) and aniline (224 mg, 2.42 mmol) in methanol (30 mL) was warmed and the methanol, which distilled over, was collected. When 10 mL of methanol had been collected, the mixture was allowed to cool and the intermediate Schiff's base crystallized out. This material was collected and redissolved in fresh methanol (30 mL). Sodium borohydride (1 molar equiv.) was added in portions and the color immediately discharged. The mixture was concentrated to 50% of its original volume, then poured into an excess of water (100 mL). The aqueous solution was rendered acidic with 2N HCl, filtered to remove any insoluble material, then basified with 7%, NaHCO3. The product, which precipitated, was collected by filtration and dried to afford 6-hydroxy-7-phenylaminomethyl-3,4-dihydrobenzopyran (277 mg, 49%), m.p. 135°-137° C.

Workup

  1. temperaturewas warmed
  2. distillationthe methanol, which distilled over,
  3. customwas collected
  4. customWhen 10 mL of methanol had been collected
  5. temperatureto cool
  6. customthe intermediate Schiff's base crystallized out
  7. customThis material was collected
  8. dissolutionredissolved in fresh methanol (30 mL)
  9. additionSodium borohydride (1 molar equiv.) was added in portions
  10. concentrationThe mixture was concentrated to 50% of its original volume
  11. additionpoured into an excess of water (100 mL)
  12. filtrationfiltered
  13. customto remove any insoluble material
  14. customThe product, which precipitated
  15. filtrationwas collected by filtration
  16. customdried

Sources & evidence

ORD record
ord-e4122300dd304b1593bedf98eb030ac4
Source dataset
uspto-grants-1986_01
Patent number
US04563476

Reaction notes

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