Sulfuric Acid → HCID 18677103, compound

HRID 1634109Notes

Reaction equation

HRID 1634109 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=O.C([N:20]1[CH:24]=CN=C1)(N1C=CN=C1)=O.C(N(CC)C(C)C)(C)C.Cl.[CH3:35][O:36]CN.S(=O)(=O)(O)O>CN(C=O)C>[CH3:35][O:36][N:20]([CH3:24])[C:10]([CH:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)=[O:12]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 5757772-Indancarboxylic AcidHCID 21959107Methoxymethanamine hydrochloride

Product 1

HCID 18677103HCID 18677103, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of indane 2-carboxylic acid (324 mg, 2 mmol) and carbonyldiimidazole (299 mg, 2.2 mmol) in DMF (5 mL) was stirred at room temperature for 30 min. N,N-diisopropylethylamine (0.522 mL, 3 mmol) was added followed by N-methoxymethyl amine hydrochloride (195 mg, 2 mmol). The reaction mixture was stirred at room temperature for 18 h, and then treated with 1N sulfuric acid (100 mL). The mixture was extracted with methylene chloride (3×50 mL), and the combined extracts were washed with water, dried over anhydrous sodium sulfate, and evaporated to give N-methoxy-N-methyl-indane-2-carboxamide as a light brownish oil which was used without further purification in the next step.

Workup

  1. extractionThe mixture was extracted with methylene chloride (3×50 mL)
  2. washthe combined extracts were washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-f8365d777124477090781c67c5b3ccb2
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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