Butanoic acid, 2-bromo-, ethyl ester → 8-bromo-2-ethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 76341

Reaction equation

HRID 76341 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[OH:9].N12CCCN=C1CCCCC2.[CH3:21][CH2:22][CH:23](Br)[C:24](OCC)=[O:25]>CN1CCCC1=O>[Br:1][C:2]1[C:3]2[O:9][CH:23]([CH2:22][CH3:21])[C:24](=[O:25])[NH:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79039Butanoic acid, 2-bromo-, ethyl esterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 155315062-Amino-6-bromophenol

Product 1

HCID 667152308-bromo-2-ethyl-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 71%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Procedure & NMR Data: 1.5 g (7.9 mmol) of 2-bromo-6-aminophenol, 1.08 ml (0.9 eq, 7.11 mmol) of 1.8-diazabicyclo[5.4.0]undec-7-ene and 3.5 mL of DL-Ethyl 2-bromobutyrate (3 eq, 23.7 mmol)) in 30 mL of 1-Methyl-2-pyrrolidinone were mixed. 1.447 g of P1 were obtained, yield 71%.

Workup

  1. custom1.447 g of P1 were obtained

Sources & evidence

ORD record
ord-efd9c31ad02147a0b0605978b604591c
Source dataset
uspto-grants-2014_09
Patent number
US08835628B2

Linked notes

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