Methyl chloroformate → Methyl 2,3-dihydro-1H-indole-1-carboxylate

HRID 2307413Notes

Reaction equation

HRID 2307413 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:11]([O:13][CH3:14])=[O:12].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:14][O:13][C:11]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)=[O:12]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 10328Indoline

Product 1

HCID 690083Methyl 2,3-dihydro-1H-indole-1-carboxylateYield 99.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of indoline (11.97 g, 0.1 mol), methyl chloroformate (15.45 mL, 0.2 mol), triethylamine (40.4 g, 0.4 mol), and DMAP (0.5 g, 0.004 mol) in CH2Cl2 (100 mL) was stirred for 16 hours. The reaction mixture was quenched with water (10 mL). The reaction was extracted with CH2Cl2 (1×40 mL). The organic layer washed with water (1×50 mL), dried over anhydrous magnesium sulfate, filtered and the resultant filtrate was concentrated in vacuo to provide the title compound (17.6 g, 99%) which was used without further purification.

Workup

  1. customThe reaction mixture was quenched with water (10 mL)
  2. extractionThe reaction was extracted with CH2Cl2 (1×40 mL)
  3. washThe organic layer washed with water (1×50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe resultant filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fb6e172a4c7c470882b10a1552740b38
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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