3-Aminobenzyl alcohol → HCID 72491609, compound

HRID 2102956Notes

Reaction equation

HRID 2102956 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].O.[N+:11]([CH:14]([CH:17]=O)[CH:15]=[O:16])([O-:13])=[O:12].[Na].C(O)(=O)/C(=C(\C=O)/Br)/Br>Cl.O>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([NH:1][CH:17]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=[O:16])[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 802933-Aminobenzyl alcoholHCID 3033972Mucobromic AcidHCID 71317419Sodium nitromalonaldehyde hydrate

Product 1

HCID 72491609HCID 72491609, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

3-Aminobenzyl alcohol (4.97 g, 0.0404 mol) was dissolved in 4 mL conc HCl. Sodium nitromalonaldehyde monohydrate (prepared from mucobromic acid according to the procedure in Organic Syntheses Vol IV, pp 844, 1963) (4.25 g, 0.0269 mol) was dissolved in 35 mL water and added to the amine solution (a yellow precipitate formed immediately)—a further 80 mL of water being added to aid stirring. After 10 min, the precipitate was filtered, washed with water and air dried overnight to give the product (4.3 g) as a yellow solid.

Workup

  1. additionadded
  2. filtrationthe precipitate was filtered
  3. washwashed with water and air
  4. customdried overnight

Sources & evidence

ORD record
ord-4e6fa05644724c83b479d4604c08a893
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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