Malonic Acid → HCID 70627355, compound

HRID 1703575Notes

Reaction equation

HRID 1703575 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:18])[CH2:17][CH2:16][CH2:15][CH:14]3[CH:10]2[CH2:11][CH2:12][NH:13]3)[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:20][CH2:21][OH:22].C(=O)([O-])[O-].[Na+].[Na+].C(O)(=O)CC(O)=O.C(O)(=O)CC([O-])=O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:18])[CH2:17][CH2:16][CH2:15][CH:14]3[CH:10]2[CH2:11][CH2:12][N:13]3[CH2:20][CH2:21][OH:22])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 5

HCID 867Malonic AcidHCID 10340Sodium CarbonateHCID 108982-BromoethanolHCID 3748644Propanedioic acid, ion(1-)HCID 70627092HCID 70627092, compound

Product 1

HCID 70627355HCID 70627355, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.8 g (3aRS,4SR,7aRS)-4-(3,4-dichlorophenyl)hexahydro-4-indolinol (see Example 3), 1.6 g 2-bromoethanol and 4 g sodium carbonate are heated for 4 hours at 100° in 50 ml dimethylformamide. The resulting mixture is evaporated to dryness, and the residue is partitioned between methylene chloride and 2N tartaric acid. The aqueous phase is made alkaline and repeatedly extracted with methylene chloride. The last-mentioned methylene chloride phase is dried over sodium sulphate, and evaporated to yield as an oily residue, the title compound in crude free base form, which is converted by addition of an equivalent amount of malonic acid, into the hydrogen malonate. M.Pt. 161°.

Workup

  1. customThe resulting mixture is evaporated to dryness
  2. customthe residue is partitioned between methylene chloride and 2N tartaric acid
  3. extractionrepeatedly extracted with methylene chloride
  4. dry with materialThe last-mentioned methylene chloride phase is dried over sodium sulphate
  5. customevaporated
  6. customto yield as an oily residue

Sources & evidence

ORD record
ord-53801852fc234f489c7b644f442fd5a3
Source dataset
uspto-grants-1978_11
Patent number
US04124719

Reaction notes

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