Dichloromethane → HCID 136341362, compound

HRID 627728Notes

Reaction equation

HRID 627728 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12]C)=[CH:7]2.B(Br)(Br)Br.ClCCl>ClCCCl>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([OH:12])=[CH:7]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 867157508-Chloro-3-methoxy-1,7-naphthyridine

Product 1

HCID 136341362HCID 136341362, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a 75 mL pressure vessel were charged with 8-chloro-3-methoxy-1,7-naphthyridine (0.8 g, 4.11 mmol) and DCE (10 ml). To this was added boron tribromide, 1.0M in dichloromethane (20.55 ml, 20.55 mmol) slowly. The brown heterogeneous mixture was stirred at RT and then was heated to 60° C. in oil bath and stirred for 3 h. It was cooled to 0° C. by ice bath and quenched with sat. Na2CO3 very slowly. Organic solvents were reduced, and 100 ml EtOH was added to the resulting residue. The white precipitate was filtered out. The filtrate was concentrated to yield 8-chloro-1,7-naphthyridin-3-ol as crude product which was used for next step directly. MS m/z: 181.2 [M+H].

Workup

  1. temperaturewas heated to 60° C. in oil bath
  2. stirringstirred for 3 h
  3. temperatureIt was cooled to 0° C. by ice bath
  4. customquenched with sat. Na2CO3 very slowly
  5. addition100 ml EtOH was added to the resulting residue
  6. filtrationThe white precipitate was filtered out
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c4698a01461946cfadd9240109f6a457
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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