Hydrochloric Acid → N-(5-Bromonaphthalene-1-carbonyl)-N-methylglycine

HRID 1904096노트

반응식

HRID 1904096 반응식
C[O:2][C:3](=[O:20])[CH2:4][N:5]([C:7]([C:9]1[C:18]2[C:13](=[C:14]([Br:19])[CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:8])[CH3:6].[OH-].[Na+].Cl>CO>[Br:19][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[CH:12]=[CH:11][CH:10]=[C:9]2[C:7]([N:5]([CH3:6])[CH2:4][C:3]([OH:20])=[O:2])=[O:8]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13318008HCID 13318008, 화합물

생성물 1

HCID 13318015N-(5-Bromonaphthalene-1-carbonyl)-N-methylglycine수율 91.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

N-[(5-Bromo-1-naphthalenyl)carbonyl]-N-methylglycine methyl ester (3.7 g, 11.0 mmoles, described in Example 2) was suspended in methanol (50 ml). A solution of 1 N aqueous NaOH (13.2 ml) was added to the suspension. The mixture was stirred at 20°-22° C. for 1.5 hr. The mixture was neutralized with aqueous HCl and concentrated under reduced pressure to remove the methanol. The residual solution was made acidic with aqueous HCl and extracted with ethyl acetate. The extract was dried (MgSO4), filtered and evaporated to dryness. The residue was crystallized from ethanol-water to give 3.25 g of the title compound; mp 205° C.; NMR (DMSO-d6) δ2.75 & 3.10 (2s, 3H), 2.75 & 3.10 (2s, 3H), 3.75 & 4.25 (2s, 2H), 7.3-8.3 (m, 6H); IR (Nujol™) 1745 with inflection at 1720, 1580 cm-1 ; UVλmax (EtOH) 322 nm (ε680), 316 (1,000), 299 (6,510), 289 (9,055), 279 (7,150) 226 (63,080); Anal Calcd: C, 52.19% H, 3.76% N, 4.35%; Found: C, 52.09% H, 38.4% N, 4.48%.

후처리

  1. concentrationconcentrated under reduced pressure
  2. customto remove the methanol
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was crystallized from ethanol-water

출처 및 근거

ORD 기록
ord-f293ae114f294f3f835e3d0508980f78
출처 데이터셋
uspto-grants-1984_03
특허 번호
US04439617

반응 노트

불러오는 중…