3-Bromoaniline → HCID 18548970, compound

HRID 1266266Notes

Reaction equation

HRID 1266266 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH3:14])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21].Cl.N1C=CC=CC=1.[NH4+].[OH-]>C(OC(O)C)C.O>[Br:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH3:14])[N:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 115623-BromoanilineHCID 14923Ammonium HydroxideHCID 10176127Pyridinium chlorideHCID 18548943HCID 18548943, compound

Product 1

HCID 18548970HCID 18548970, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 101298981-EthoxyethanolSolvent

Procedure

4-Chloro-6-ethoxyl-[1,5]naphthyridine-3-carbonitrile (500 mg, 2.14 mmol) was heated at reflux with m-bromoaniline (0.69 ml, 3 eq) in the presence of pyridine HCl salt (250 mg, 1.1 eq) in ethoxyethanol (20 ml) under argon for 3 hrs. After cooling the mixture was diluted with water, made basic with NH4OH, and extracted with CH2Cl2. The extracts were washed (Brine), dried (Na2SO4), and concentrated. The remaining solid was triturated with a mixture of CH2Cl2 and ether, giving the title compound as a yellow solid. mass spectrum (electrospray, m/e): 370.9 (M+H); IR cm-1: 3305, 2217; H-NMR δ (DMSO-d6): 1.365 (3H, t, CH3), 4.585 (2H, q, CH2), 7.327 (1H, d, C8-H), 7.395 (2H, m, C4′ and C6 Hs in bromoaniline), 7.503, (1H, m, C5′-H), 7.618 (1H, s, C2′-H), 8.194 (1H, d, C7-H), 8.516 (1H, s, C2-H), 9.684 (1H, bs, NH).

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted with CH2Cl2
  3. washThe extracts were washed (Brine)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe remaining solid was triturated with a mixture of CH2Cl2 and ether

Sources & evidence

ORD record
ord-30864b70f6d84a4e9d55bde3f1d1a0dc
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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