Benzaldehyde → HCID 86735312, compound

HRID 462099Notes

Reaction equation

HRID 462099 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH:5]([C:9]1[CH:14]=[CH:13][C:12]2[O:15][CH2:16][O:17][C:11]=2[CH:10]=1)[C:6]([OH:8])=[O:7].[OH-].[Na+].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH4-].[Na+].Cl>O>[CH2:20]([NH:2][CH2:3][CH2:4][CH:5]([C:9]1[CH:14]=[CH:13][C:12]2[O:15][CH2:16][O:17][C:11]=2[CH:10]=1)[C:6]([OH:8])=[O:7])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 859474224-Amino-2-(2H-1,3-benzodioxol-5-yl)butanoic acid--hydrogen chloride (1/1)

Product 1

HCID 86735312HCID 86735312, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of 26 g of the amino acid hydrochloride prepared in Example 5 (0.1 mole), in 80 ml of water, was added 8.4 g of sodium hydroxide (0.21 moles), in 42 ml of water, followed by 11.7 g (0.11 moles) of benzaldehyde. The initially turbid mixture immediately cleared. After one hour, the mixture was evaporated to a thick syrup on the rotary evaporator, the syrup dissolved in 75 ml of ethanol, and the evaporation to syrup repeated. The residue was dissolved in 500 ml of methanol and 6.5 g of sodium borohydride (0.17 moles) added in several portions. After stirring for 1.5 hours, the solvent was removed on the rotary evaporator, leaving a grayish solid. This residue was dissolved in 200 ml of water and 10 percent hydrochloric acid added to pH 7. The precipitate which formed was collected by filtration, washed with water, and dried to yield the above-named product, m.p. 217°-218° dec.

Workup

  1. customthe mixture was evaporated to a thick syrup on the rotary evaporator
  2. dissolutionthe syrup dissolved in 75 ml of ethanol
  3. customthe evaporation to syrup
  4. dissolutionThe residue was dissolved in 500 ml of methanol
  5. customthe solvent was removed on the rotary evaporator
  6. customleaving a grayish solid
  7. customThe precipitate which formed
  8. filtrationwas collected by filtration
  9. washwashed with water
  10. customdried
  11. customto yield the above-named product, m.p. 217°-218° dec.

Sources & evidence

ORD record
ord-15cd324eb05f40c18f1b16c81cab0a18
Source dataset
uspto-grants-1977_12
Patent number
US04065473

Reaction notes

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