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Chloroacetyl chloride → HCID 22350167, compound

HRID 2224605
Notes
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Reaction equation

HRID 2224605 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[NH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5]2.[O:16]1CC[CH2:18][CH2:17]1.C(=O)([O-])O.[Na+].ClCC(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>>[O:16]=[C:17]1[CH2:18][O:11][C:10]2[CH:9]=[C:8]3[NH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5][C:4]3=[CH:3][C:2]=2[NH:1]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 22350178Methyl 5-amino-6-hydroxy-indole-2-carboxylate

Product 1

HCID 22350167HCID 22350167, compoundYield 71.2%

Procedure

To a solution of 2.0 g (9.7 mmol) of methyl 5-amino-6-hydroxy-indole-2-carboxylate (Example 5/c) in 300 ml of tetrahydrofuran 2.45 g (29.2 mmol) of sodium hydrogencarbonate and 1.3 ml (16.3 mmol) of chloroacetyl chloride are added and the mixture is stirred at room temperature overnight. The reaction mixture is concentrated and 100 ml of water is added to the residue. The precipitated crystalls are filtered off, washed with water and suspended in 120 ml of acetonitrile. 4.05 g (29.3 mmol) of potassium carbonate is added to the suspension and the resulted mixture is stirred at room temperature overnight. The reaction mixture is concentrated and 100 ml of water is added to the residue. The product is filtered off, washed with water and dried to yield 1.7 g (71%) of the title compound. Mp.: 188-196° C. (water).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. addition100 ml of water is added to the residue
  3. filtrationThe precipitated crystalls are filtered off
  4. washwashed with water
  5. stirringthe resulted mixture is stirred at room temperature overnight
  6. concentrationThe reaction mixture is concentrated
  7. addition100 ml of water is added to the residue
  8. filtrationThe product is filtered off
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-535e4f831337444b8243364d7add37b5
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07378431B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes