4-Hydroxybenzaldehyde → HCID 70490905, compound

HRID 464332Notes

Reaction equation

HRID 464332 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[C:21]([O:12][C:13]1[CH:20]=[CH:19][C:16](/[CH:17]=[C:6]2\[CH2:7][CH2:8][CH2:9][C:10]3[CH:11]=[C:2]([CH3:1])[CH:3]=[N:4][C:5]\2=3)=[CH:15][CH:14]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 7918Acetic AnhydrideHCID 1200283-Methyl-5,6,7,8-tetrahydroquinoline

Product 1

HCID 70490905HCID 70490905, compound

Procedure

5,6,7,8-Tetrahydro-3-methylquinoline (6.6 g) was dissolved in acetic anhydride (10 ml) and 4-hydroxybenzaldehyde (7.35 g) was added. The mixture was allowed to reflux for 18 hours after which the solvent was removed under reduced pressure. The residue was added to 1M NaOH (300 ml) and the solid extracted with dichloromethane (3×150 ml) and dried (Na2SO4). Solvent was removed under reduced pressure. The solid residue was recrystallised from ethyl acetate to give the title compound (4.5 g). m.p. 119°-122° C.

Workup

  1. temperatureto reflux for 18 hours after which the solvent
  2. customwas removed under reduced pressure
  3. additionThe residue was added to 1M NaOH (300 ml)
  4. extractionthe solid extracted with dichloromethane (3×150 ml)
  5. dry with materialdried (Na2SO4)
  6. customSolvent was removed under reduced pressure
  7. customThe solid residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-e4252ed03ca144959fa3b9d0c6a9beb8
Source dataset
uspto-grants-1985_10
Patent number
US04547510

Reaction notes

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