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Water → 6-nitro-2,2-dimethyl-3-(methoxycarbonylamino)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

HRID 2399326
Notes
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Reaction equation

HRID 2399326 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH2:15][NH2:16])=[C:9]([N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]3=[O:23])[C:8]=2[CH:24]=1)([O-:3])=[O:2].C(N(CC)CC)C.Cl[C:33]([O:35][CH3:36])=[O:34].O>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH2:15][NH:16][C:33]([O:35][CH3:36])=[O:34])=[C:9]([N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]3=[O:23])[C:8]=2[CH:24]=1)([O-:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 193870526-nitro-2,2-dimethyl-3-aminomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

Product 1

HCID 193871646-nitro-2,2-dimethyl-3-(methoxycarbonylamino)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyranYield 56%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-nitro-2,2-dimethyl-3-aminomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran (0.53 g, 1.53 mmol) and triethylamine (0.25 ml, 1.80 mmol) in dichloromethane (10 ml) at room temperature was added methyl chloroformate (0.14 ml, 1.80 mmol). The solution was stirred for 2 hours and then water added. The organic layer was separated, dried and evaporated to give a crude product, which was crystallized from ether. The crystalline material was then purified by chromatography on silica gel, eluting with acetone/dichloromethane (20/80) to give 0.33 g of 6-nitro-2,2-dimethyl-3-(methoxycarbonylamino)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 199° C.

Workup

  1. customThe organic layer was separated
  2. customdried
  3. customevaporated
  4. customto give a crude product, which
  5. customwas crystallized from ether
  6. customThe crystalline material was then purified by chromatography on silica gel
  7. washeluting with acetone/dichloromethane (20/80)

Sources & evidence

ORD record
ord-90c3f3dbc50a4d48a57f4d06d8c6f461
Source dataset
uspto-grants-1995_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05447943

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes