Sodium Hydroxide → HCID 70298353, compound

HRID 1004083Notes

Reaction equation

HRID 1004083 reaction equation
C([O:3][C:4]([C:6]1([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH:14]=[C:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][CH2:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[ClH:36].[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([C:6]2([C:4]([OH:5])=[O:3])[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH:14]=[C:15]3[C:16]4[CH:29]=[CH:28][CH:27]=[CH:26][C:17]=4[CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]3=4)[CH2:8][CH2:7]2)=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50852557HCID 50852557, compound

Product 1

HCID 70298353HCID 70298353, compoundYield 165.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the above ester (2.20 g, 0.0044 mol) and 20% sodium hydroxide (2 ml) in ethanol (18 ml) was stirred at room temperature for 24 h and left standing for additional 24 h. Ethanol was evaporated in vacuo and the residue was dissolved in dichloromethane (300 ml). The resulting solution was acidified with acetic acid, washed with water (3×15 ml) and the organic phase was dried (MgSO4). The solvent was evaporated in vacuo, the residue (2.60 g) was dissolved in a mixture of ether and acetone (1:1, 20 ml) and the solution was made acidic with a solution of hydrogen chloride in ether. The solvents were evaporated in vacuo, the amorphous residue was twice dissolved in acetone (20 ml) and re-evaporated in vacuo. The solid was suspended in dry ether (100 ml) and stirred at room temperature for 3 h. The precipitate was filtered off and dried in vacuo, affording 1.85 g (82%) of the title compound.

Workup

  1. waitleft
  2. waitstanding for additional 24 h
  3. customEthanol was evaporated in vacuo
  4. dissolutionthe residue was dissolved in dichloromethane (300 ml)
  5. washwashed with water (3×15 ml)
  6. dry with materialthe organic phase was dried (MgSO4)
  7. customThe solvent was evaporated in vacuo
  8. dissolutionthe residue (2.60 g) was dissolved in a mixture of ether and acetone (1:1, 20 ml)
  9. customThe solvents were evaporated in vacuo
  10. dissolutionthe amorphous residue was twice dissolved in acetone (20 ml)
  11. customre-evaporated in vacuo
  12. stirringstirred at room temperature for 3 h
  13. filtrationThe precipitate was filtered off
  14. customdried in vacuo

Sources & evidence

ORD record
ord-1d825fe42e9940029cc4e5cefeb7f855
Source dataset
uspto-grants-2000_04
Patent number
US06048856

Reaction notes

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