Acetyl chloride → HCID 86613188, compound

HRID 642679Notes

Reaction equation

HRID 642679 reaction equation
[C:1]([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:14])[CH:12]=2)[N:7]([CH2:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)C=1C(O)=O)([OH:3])=[O:2].[C:29](Cl)(=[O:31])[CH3:30]>>[F:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:15][C:16]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=1)[C:30]1[C:29](=[O:31])[O:3][C:1](=[O:2])[CH2:4][C:5]2=1

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 235828103-(Carboxymethyl)-5-fluoro-1-(naphthalen-1-ylmethyl)-1H-indole-2-carboxylic acid

Product 1

HCID 86613188HCID 86613188, compound

Procedure

A mixture of 3-carboxymethyl-5-fluoro-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid (from Example 33, 0.5 g) in acetylchloride (6.2 ml) was heated to reflux for 5 h. The solution was evaporated and the residue triturated with diethylether to give 6-fluoro-9-naphthalen-1-ylmethyl-4,9-dihydro-pyrano[3,4-b]indole-1,3-dione as a pale yellow solid. MS: 377.4 ([M+NH4]+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h
  3. customThe solution was evaporated
  4. customthe residue triturated with diethylether

Sources & evidence

ORD record
ord-435df657cc1a4d399ddaaf0ef05892b3
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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