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

HRID 247197ノート

反応式

HRID 247197 の反応式
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]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13318008HCID 13318008、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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 1N 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) δ 2.75 & 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 ; UV λmax (EtOH) 322 nm (ε 680), 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%.

後処理

  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

出典と根拠

ORDレコード
ord-71a7d1610bcf4a53998438f33412e256
出典データセット
uspto-grants-1987_11
特許番号
US04705882

反応ノート

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