Acetaldehyde → HCID 58574749, compound

HRID 1619423Notes

Reaction equation

HRID 1619423 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[N:5]=[C:4]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:3]12.[CH:21](=O)[CH3:22].CC(O[Na])=O.C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[CH:21](=[C:15]1/[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:3]2[C:2](=[O:1])[C:11]3[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=3)[N:5]=[C:4]/12)/[CH3:22]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 10340Sodium CarbonateHCID 71306156,8,9,10,11,13-Hexahydro-13-oxo-7H-azocino[2,1-b]quinazoline-3-carboxylic acidHCID 178418247HCID 178418247, compound

Product 1

HCID 58574749HCID 58574749, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 13-oxo-7,8,9,10,11,13-hexahydro-6H-azocino[2,1-b]quinazoline-3-carboxylic acid (100 mg, 0.37 mmol), acetaldehyde (5 mL) and CH3COONa (1 g) in acetic acid (10 mL) was stirred at 110° C. for 24 hours. After it was cooled to room temperature, the mixture was adjusted to pH around 8 with Na2CO3 and extracted with a mixture of dichloromethane/methanol (10/1) (3×30 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude product obtained was used for the next step without further purification.

Workup

  1. extractionextracted with a mixture of dichloromethane/methanol (10/1) (3×30 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-06730f6f82374f7894042bb3024f42c0
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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