Isopropylamine → HCID 21440618, compound

HRID 328872Notes

Reaction equation

HRID 328872 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:18]([CH:20]=O)=[O:19])[CH:12]=[C:13]([C:15]([OH:17])=[O:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22]([NH2:25])([CH3:24])[CH3:23]>CO>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:12]=[C:11]([CH:18]([OH:19])[CH2:20][NH:25][CH:22]([CH3:24])[CH3:23])[CH:10]=1)[C:15]([OH:17])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 21440620HCID 21440620, compound

Product 1

HCID 21440618HCID 21440618, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 3-benzyloxy-5-carboxyphenylglyoxal (;b 120 moles) was dissolved in MeOH (1 l.) and cooled to 0°. Isopropylamine (200 ml) was added at 0° and the resulting mixture was stirred at 0° for 1 hr. before KBH4 (12.2 g, 228 moles) was added over a period of 2 hrs., portionwise. The resultant mixture was allowed to stir at room temperature overnight before it was evaporated to a residual glass. The residue was acidified with 6N HCl (1 l.) and extracted with CHCl3 (1 142 l.). The solid HCl precipitated from the CHCl3 extract upon standing; yield 21.9 g which gave 20.0 g (50%) mp. 290°- 292° dec. of the free base upon stirring in aqueous NH4OH and collecting by filtration.

Workup

  1. temperaturecooled to 0°
  2. stirringto stir at room temperature overnight before it
  3. customwas evaporated to a residual glass
  4. extractionextracted with CHCl3 (1 142 l.)
  5. customThe solid HCl precipitated from the CHCl3
  6. extractionextract

Sources & evidence

ORD record
ord-acb5a8e3dcfa49a1ac8af909420e039e
Source dataset
uspto-grants-1977_04
Patent number
US04018825

Reaction notes

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