Formaldehyde → HCID 86723957, compound

HRID 1475339Notes

Reaction equation

HRID 1475339 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[CH2:10][C:9]1=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19](=[O:22])([O-])[O-].[K+].[K+].C=O.[C:27]([O-])(O)=[O:28].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([CH2:19][OH:22])([CH2:27][OH:28])[C:9]1=[O:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 60153287HCID 60153287, compound

Product 1

HCID 86723957HCID 86723957, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (2.7 g, 10.1 mmol), potassium carbonate (4.2 g, 30.3 mmol), THF (150 mL) and paraformaldehyde (7.2 g, 0.24 mol) was stirred at 20° C. for 2 h then was poured onto ice (100 g) and saturated aqueous NaHCO3 (100 mL) and extracted with EtOAc (4×100 mL). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo. Chromatography (SiO2; gradient elution with 30-100% EtOAc in petrol) gave an orange solid (3.7 g). Crystallisation from EtOAc and petrol gave the title compound (1.23 g). Chromatography of the mother liquor gave further product (0.978 g). MS: [M-tert-Bu]+=272 (fragment ion).

Workup

  1. extractionextracted with EtOAc (4×100 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. customevaporated in vacuo
  4. washChromatography (SiO2; gradient elution with 30-100% EtOAc in petrol)

Sources & evidence

ORD record
ord-e103ff060e7c4b02944a7ce6d84cae42
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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