Oxalyl chloride → (R)-3-cyclohexyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid chloride

HRID 500447Notes

Reaction equation

HRID 500447 reaction equation
[CH:1]1([C@H:7]2[N:12]3[CH:13]=[C:14]([C:19]([OH:21])=O)[C:15]4[CH:16]=[CH:17][CH:18]=[C:10]([C:11]=43)[O:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:25])=O>ClCCl>[CH:1]1([C@H:7]2[N:12]3[CH:13]=[C:14]([C:19]([Cl:25])=[O:21])[C:15]4[CH:16]=[CH:17][CH:18]=[C:10]([C:11]=43)[O:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 68675192(R)-3-cyclohexyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid

Product 1

HCID 87537363(R)-3-cyclohexyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-cyclohexyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid (362 mg, 1.23 mmol) in dichloromethane (20 ml) was added oxalyl chloride (0.215 ml, 2.46 mmol). The deep blue mixture was stirred at room temperature for 2 h and then the solvent was removed in vacuo to afford (R)-3-cyclohexyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid chloride (380 mg, 1.23 mmol) as a blue solid.

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c5ee5a33761f4031b7f742dc626c56e5
Source dataset
uspto-grants-2010_08
Patent number
US07772227B2

Reaction notes

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