3-Aminobenzyl alcohol → HCID 72491609, compound

HRID 970658Notes

Reaction equation

HRID 970658 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-9b5cac68450449119edcef15d1b094d4
Source dataset
uspto-grants-2007_12
Patent number
US07312233B2

Reaction notes

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