Hydrogen Bromide → HCID 67503082, compound

HRID 219290Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[N:5][C:6]2[CH:7]=[CH:8][N:9]([CH:14]([CH3:20])[C:15]([O:17]CC)=[O:16])[C:10](=[O:13])[C:11]=2[CH:12]=1.[BrH:21]>>[BrH:21].[OH:2][C:3]1[CH:4]=[N:5][C:6]2[CH:7]=[CH:8][N:9]([CH:14]([CH3:20])[C:15]([OH:17])=[O:16])[C:10](=[O:13])[C:11]=2[CH:12]=1

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 58015497HCID 58015497, compound

Product 1

HCID 67503082HCID 67503082, compoundYield 100.5%

Conditions

Temperature: 130 °C

Procedure

A resealable pressure-resistant bottle was charged with ethyl 2-(3-methoxy-5-oxo-1,6-naphthyridin-6(5H)-yl)propanoate (0.83 g, 3.0 mmol) (Example 515) and conc. HBr (0.16 ml, 3.0 mmol). The vessel was sealed and the mixture was stirred at 130° C. for 20 hours. The reaction mixture was then concentrated to afford 2-(3-hydroxy-5-oxo-1,6-naphthyridin-6(5H)-yl)propanoic acid hydrobromide (0.95 g, 100% yield) as brown solid. This was carried through crude in the next step. Free base material MS m/z=235.0 [M+1]+. Calc'd for C11H11BrN2O4: 315.1.

Workup

customThe vessel was sealed
concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record: ord-7156baa22f564c00a348db5a976e8a1d
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198448B2

Reaction notes

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