Water → HCID 13577659, compound

HRID 1589210Notes

Reaction equation

HRID 1589210 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][C:5]([Cl:16])=[CH:4][C:3]=1[CH2:17][C:18](OCC)=[O:19].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:1][C:2]1[C:7]([CH:8]([OH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][C:5]([Cl:16])=[CH:4][C:3]=1[CH2:17][CH2:18][OH:19]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13577656HCID 13577656, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13577659HCID 13577659, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 15.85 g (0.05 mole) of 2-amino-3-benzoyl-5-chlorobenzeneacetic acid, ethyl ester dissolved in 100 ml of dry tetrahydrofuran was added dropwise to a suspension of 4.0 g (0.105 mole) of lithium aluminum hydride in 50 ml of dry tetrahydrofuran. Gentle reflux was maintained during the addition. Reflux was continued for 2 hours after completion of the addition. The mixture was cooled and carefully treated with 4 ml of water, 4 ml of 15% sodium hydroxide and 12 ml of water. The resulting mixture was filtered, the filtrate stripped and the resulting residue recrystallized from toluene. The titled compound, 10.5 g (70%) having a m.p. of 130°-132° C. was obtained.

Workup

  1. temperatureGentle reflux
  2. temperaturewas maintained during the addition
  3. temperatureReflux
  4. additionafter completion of the addition
  5. temperatureThe mixture was cooled
  6. filtrationThe resulting mixture was filtered
  7. customthe resulting residue recrystallized from toluene
  8. customwas obtained

Sources & evidence

ORD record
ord-407d037d476946e0858e390a2667ff4e
Source dataset
uspto-grants-1986_02
Patent number
US04568695

Reaction notes

Loading…