Acetic Acid → HCID 18671407, compound

HRID 1057510Notes

Reaction equation

HRID 1057510 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.[NH2:13][CH2:14][CH2:15][CH2:16][OH:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4][NH:13][CH2:14][CH2:15][CH2:16][OH:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 90863-Amino-1-propanolHCID 5049666Sodium triacetoxyborohydrideHCID 111389422-Bromo-5-nitrobenzaldehyde

Product 1

HCID 18671407HCID 18671407, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-bromo-5-nitrobenzaldehyde (1 eq) in methylene chloride (0.1 M) at room temperature was added 3-amino-1-propanol (2 eq). After stirring for 4 hr, sodium triacetoxyborohydride (2 eq) and acetic acid (5 eq) was added. The reaction mixture was stirred for 3 hr and carefully quenched with methanol. The organic phase was washed with saturated sodium bicarbonate and brine. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated in vacuo and purified by flash chromatography (10% EtOAc/Hexane). EI-MS m/z 289 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for 3 hr
  2. customcarefully quenched with methanol
  3. washThe organic phase was washed with saturated sodium bicarbonate and brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (10% EtOAc/Hexane)

Sources & evidence

ORD record
ord-198aa65d9ac5400c9deb4c3387925149
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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